April 28, 2022

154 Building a Thriving Organization by Helping Clients Implement OKRs, Achieve Better Alignment and Strategy Execution with Workboard CEO Deidre Paknad | Partnering Leadership Global Thought Leader

154 Building a Thriving Organization by Helping Clients Implement OKRs,  Achieve Better Alignment and Strategy Execution with Workboard CEO Deidre Paknad | Partnering Leadership Global Thought Leader

In this episode of Partnering Leadership, Mahan Tavakoli speaks with Deidre Paknad, co-founder and CEO of WorkBoard and founder of Results Foundry. Deidre Paknad shared her journey leading to her success as the founder of three start-ups. Deidre also talked about her founding of Workboard and how the organization supports its clients to execute their strategy faster by effective implementation of OKRs.   Deidre Paknad also shared her thoughts on the future of work and what organizations can do to thrive through uncertainty.

Some highlights:

- What led Deidre Paknad to become an entrepreneur

- The challenges faced by the first time entrepreneur 

- Deidre Paknad on the advantages and disadvantages of working at IBM 

- The origin story of Workboard

- Deidre Paknad being told that she has three strikes against her

- How Workboard helps companies achieve alignment through OKRs 

- How the pandemic sped up the pace of change 

- Deidre Paknad's advice on how to get every member of an organization to focus

- Deidre on the leadership capabilities that are required throughout the organization.

- How to transform a culture of complacency into a culture of ambition 

- Deidre Paknad on facing personal and business challenges as a CEO during the pandemic

- How presence can help unlock an organization's potential  




- Larry Robertson (Listen to the Partnering Leadership conversation with Larry Robertson)

- Azeem Azhar (Listen to the Partnering Leadership conversation with Azeem Azhar)

- Sarah Stein Greenberg (Listen to the Partnering Leadership conversation with Sarah Stein Greenberg)

- John Doerr, chairman of Kleiner Perkins and the author of Measure What Matters

- Daniel Kahneman, Nobel Prize-winning economist, and psychologist

Connect with Deidre Paknad:

WorkBoard Website

OKR Podcast 

Deidre Paknad on Twitter

Deidre Paknad on LinkedIn

Connect with Mahan Tavakoli:



More information and resources available at the Partnering Leadership Podcast website: 




[00:00:00] Mahan Tavakoli:
Welcome to partnering leadership. I'm really excited this week to be welcoming Deidre Paknad. Deidre is a co-founder and CEO of Workboard an organization that helps their customers execute on their strategy faster. We spent some time in this conversation talking about Deidre's own leadership, which I find to be inspiring and impactful.

And also, about OKR objectives and key results, which is part of what Workboard enables organizations to effectively implement and use in order to execute on their strategy more effectively and faster. So I really enjoyed this conversation, learned a lot from Deidre, and I am sure you will too. 

I also enjoy hearing from you. Keep your comments coming. mahan@mahantavakolicom. There's also a microphone icon on partnering leadership.com. Really enjoy getting those voice messages. Don't forget to follow the podcast, Tuesday conversations with magnificent change-makers from the greater Washington, DC DMV region, and Thursday conversations with brilliant global thought leaders like Deidre.

Now here's my conversation with Deidre Paknad.

Deidre Paknad, welcome to partnering leadership. I am thrilled to have you in this conversation with me. 

[00:01:23] Deidre Paknad:
Likewise, I'm so happy to be talking with you. 

[00:01:26] Mahan Tavakoli:
Deidre, you you've done a magnificent job as the CEO of three different tech startups, and now Workboard, I can't wait to get to that conversation. Before we do though, would love to know whereabouts you grew up and how your upbringing impacted the kind of person and leader you've become.

[00:01:44] Deidre Paknad:
I am originally from central California, a town called Stockton, which is not often noted as the home of startup entrepreneurs or the birthplace of that. My great, great, great grandparents went to the central valley in a covered wagon generations ago to be farmers and ranchers growers. And that's the kind of the backdrop to the life I led for semi agricultural upbringing and pretty early in my life decided while I was from Stockton, I didn't want to continue to live in Stockton. And what else was out in the world, and that, bolted me to now this landing place. 

[00:02:19] Mahan Tavakoli:
Deidre, what got you to leave Stockton at such an early age? 

[00:02:24] Deidre Paknad:
Pre-internet obviously, because if you've done three startups, you're not 25 So pre-internet, like the models for what you could be when you grew up or like really represented on TV.

If you're a girl in Stockton at the time, and maybe many places still, you can be like a nurse or a teacher. If you're a boy, it could be a fireman or a lawyer or a doctor. Those are not very exciting choices. First I'm going to skip the boy girl options, I'm going to choose from all five, like, okay. I think I'm not going to be a doctor. Okay, maybe a lawyer. Yes. I like to write, I like to argue, I'm pretty logical. I can see every side of every argument, I'm fiercely competitive, so that's my sport. I'm going to go be a lawyer. 

And so the big idea was how do I move myself to a place where I could, if you will control my own destiny financially, I could have options in my life that were greater than the options that I could see around me in both my own family and in the neighborhood and the environment that I was from.

 And the dynamic, of the situation for me was my father had died in military service when I was 10 days old, which tells you, the riches and to which I was born. But part of that aftermath of that was that the VA has an education benefit for survivors of people killed in service. And that education benefit would pay for, if I went to a university that was mistake, they would pay for the whole thing, and if I went to a private university, they would pay for part of it. I said okay. they wouldn't do that to us 22. If I graduate from high school and I'm 16, I can be, graduate from college By the time I'm 19, I can be out of law school with those benefits because there was no other way for me to get to school.

 It was not a world where you look on the internet and you find out all the options right. And there just weren't a ton of options. like first big scrappy move, let me put it that way, which was try to optimize for kind of my only route to a university, my only route to professional life with no open economic options for myself.

[00:04:24] Mahan Tavakoli:
And you took that only route, you got into law school with your first year in law school, you decided not to continue at law school. 

[00:04:32] Deidre Paknad:
I said I was going to be a lawyer. I went all in. I interned with judge, I like all of my internships in college were about law and the DA's office, like maniacally focused on that. 

First day of law school I'm in the ethics class, and the professor says, you all think that this is about justice. This is about winning or losing it that, oh, wait.

I had an internship at law school to pay my rent, where I sat in this little video booth and I videotaped third year students practicing telling clients what their rates were. And I literally sat in his dark room and I watched third year students say over and over and over again, my rate is 7 75 an hour, whatever it was, and I thought, oh my God, this is not for me.

It was torturous actually a changed directions because I had been so committed. I mean maniacally committed to go graduate everything two years early and just like rush through, that it's a pretty tough moment. Like, okay, well, if I'm not going to be that, what the heck am I going to be when I grow up? But it was an awesome decision to change. 

[00:05:38] Mahan Tavakoli:
That decision to change though, eventually you ended up becoming an entrepreneur and starting a company with your business partner and life partner Daryoush, how did you meet him? 

[00:05:52] Deidre Paknad:
Met at work, I'm with the marketing team, and he was in the product engineering team, and we quite literally met at the copy machine on my first day.

 And I don't know, maybe three months later. We were dating out to dinner, talking about, we should start a company someday, and we were young at the time, but that, I'll call it adjacency, right? Like what, he was good at, what he cared about, what he was passionate about was just pretty seamless with where my interest in, what I was patched about, what I was capable of.

And we didn't know what company we would start, but we made up this name for it. And we said, okay, some day, we're going to start a company together and be partners. and obviously we did actually twice, but it was many years later that we actually brought that to fruition, but where our edges meet is super complimentary professionally, and what we care about personally, I'll call it our moral compass and moral centers, our appetite to really leave it all on the field, those are super similar between the two of us.

[00:06:48] Mahan Tavakoli:
 That is beautiful how you complete each other in so many senses Deidre, a lot of people have difficulty holding onto a relationship, let alone when that relationship is also a work partnership, you've been able to do that well along with Daryoush.

 You started out that first company when you were in your early thirties with him raised lots of money going into 2000 and brought in a CEO. What happened then? 

[00:07:16] Deidre Paknad:
By the time we entered 2000 by today's standards, I raised a lot of money. But in those days it was, the common habit was it probably to you get it started and then you bring in a professional CEO who knows how to sales. And I did not know how to do that. In fact, I made really tragic mistakes in scaling sales. Like I could sell anything, I just didn't not build in the organization, sales competency widely. And so it was super, super tethered to my showing up in a deal and it just did not recognize how catastrophic that actually is in practice. But I knew I did not know how to build deep bend sales competency. And I'll say the amount of mentorship and guide available in the market was super anemic. It wasn't like I could look left and right, and get the answers.

And so I thought, okay, let me hire somebody who knows how to do this next stage of the company. I went to the board. The first reaction was like, no, okay. Let's work together on this. then we hire CEO coming into 2000. So like, I think that person started probably, I don't know, we had a spring event, March issue or something like that, right at the moment where scaling was no longer the issue, in fact, being really scrappy. Founder entrepreneur willing to, both sell the deals and take out the garbage, turned out to be super important, but we'd already made that transition and it was tough 

[00:08:35] Mahan Tavakoli:
Not succeeding and having a business not do well, including and most especially one that was your baby is really hard.

 What did you take out of that experience Deidre?

[00:08:48] Deidre Paknad:
I think I'm an all-in person I'm done even vaguely like a fence sitter. And I care a lot about the outcomes in every case. The first at a personal level, and obviously the kind of the first big crash and burn it's pretty devastating actually.

And time was really, really important in taking away the lessons from it where like with more distance you the, okay, you know what, here in this, right. The distribution relationships was wicked smart. The technology we had, super vissionary. Too soon, like the product was SharePoint in 2000, wasn't ready for SharePoint in 2000.

But we got the idea damn right. really big distribution partnerships with ADP and into it. And Adobe, which were fantastic. By sales scaling model, I believe that. Culture, oh, we nailed it. the lessons learned were like, not just what went wrong, but also what went right and first time entrepreneurs, you not only do you not know what you're doing wrong, you don't even know what you're doing right. I'll call it, settle in and just move on with confidence, and carrying that into the next company where I was a turnaround CEO was super helpful. Culture wow it's going to be passion filled and people are going to tare, and I am going to care and I'm going to build a sales machine full stop going to build a sales machine. That was the company that ended up being acquired by IBM. That worked quite well. 

[00:10:10] Mahan Tavakoli:
You did build that sales machine that as you mentioned, was acquired by IBM. you also had to operate within IBM, which is a very different challenge than running your own organization. What were the challenges you faced in running this unit within IBM? 

[00:10:29] Deidre Paknad:
There were some really awesome upsides that I didn't see coming. Like I had no aspiration to like work at IBM when I grew up. That wasn't the prevailing mindset and silicone valley at the time. Let's put it that way. So I did not have high expectations going in. It's important to say that there were also things that just wildly exceeded my expectations about the opportunities.

That left an indelible mark for me as well. And one of those is the incredibly level playing field for women in that company. And I had never seen a level playing field before in my lifetime. And it was a shock to actually see what it looked like. And by level playing field, I don't mean the CEO is a woman at the time, I mean, at every single level and layer of the company and of decision-making, there was equity and inclusion. And that was stunning. I didn't know what I couldn't see before. It was shocking. And it was important thing for me to take forward with me. And the other thing that I understood in a whole new way was what a really at scale distribution machine can really do.

 And that was impressive. And when I figure out how to get that distribution chain machine to work for my business, ridiculous. We grew the business so incredibly fast by understanding the route to market model, the economic machinery. And I'd never seen grow that fast. And it was really fun. I mean, wildly fun.

 The third is what a brand, how powerful a brand is to getting you the right audience. The meeting I was having with the VP of so-and-so, now I'm meeting with the CEO, the COO, and the CIO of fortune 50 and straight route to the decision suite. Those were the really big learnings that were positive experiences, you know, the negative experiences that were actually of course the friction involved in the matrix, but actually that friction, I understand why it existed. People have to drive the business. And so the friction is I need to know where you're going and I need to know where you are now for this part of the matrix.

 And then the other part of the matrix. I need to know where you are and where you're going. And so you spend all your time kind of servicing that question set. Where are you going? Where are you now? All year. And first I hated it. And then I thought, well, he can't drive blind. Obviously they need to know that.

 And then that you can't drive blind. Where are you going? Where are you now that led to this fight. This is a process. And it should work perfectly at every single company we're going to go solve this problem. And that led to work for it actually. even the friction was a positive experience for me.

 Oh, this is so solvable, so solvable. And if we solve the friction, all of that capacity, it all goes to value creation. It all goes to growth. Instead of servicing the question, where are you going? And where are you now? 

[00:13:17] Mahan Tavakoli:
What a beautiful insight Deidre, I spoke to Larry Robertson who has written a bunch of books, including one on entrepreneurship of deliberate pause.

 And he talks about the fact that entrepreneurs aren't seeking to start organizations or companies. They are people that get frustrated with a need that exists where they don't see a solution to that need. And it's that frustration that leads them to start the organization. So the frustration you were facing with the friction part in IBM is what gave you the idea for Workboard.

 Now, before we talk about that, as you were trying to raise funds, this is back in 2016, 2017. You were told by venture capitalists of the three strikes that you had against you. 

[00:14:10] Deidre Paknad:
That's right. Yeah. That was not a great day. And you know, 2016, it might've been early 2017. It was sort of the me too movement for people like me, for women entrepreneurs, there was a very real lift and leveling that came out of that. And before that, I would have said that in 2016, early 2017, the fundraising climate for me as a woman, entrepreneur was worse than the fundraising climate for me, when I raised money in September 2000, 5 months after the crash, that's saying something about how there was so little progress in the valley, in those two decades.

But the three strikes conversation was I raised a seed like 2.7 5 million and raise that from investors in the company IBM bought I'd closed the money before I was out of IBM. We had a good kind of tailwind head into the company. We had early traction. We were just short of probably a million in ARR at the time was raising which is, let's go do a series A and so I met with these investors course, super time consuming.

 And then the senior partner meets with me and he says, I like you. So I'm going to tell you the truth here. You've got three strikes against you. First, you're a woman. Second you're old. And third you're married to your co-founder. But I like you, so I want to help you anyway. And then he proceeded to offer me the exact same post or pre money as my seed round.

I want to tell you what I have to say, I know this is a broadcast, but it wasn't pretty, it wasn't pretty. And the whole takeaway is like, can I change my gender? No, can I change my age? Nope. Am I going to change my marital status for you? Hell No, and it was just is a shocking remark. And I, way I looked at it at the time, He felt so entitled that he could just say out loud what I'm guessing, others also thought, and there's real friction. 

If you happen to be me, a woman, you just layered on in my case. And if you think about that, if I was a man, who'd been a turnaround CEO that had been completely written off by its investors. It created a category, got bought by IBM that grew it 60% year over year inside a machine shrinking by 10% year over year, who would I have had a hard time getting fun? At the time, I might've been like close to 50. Would I have struggled? Hell no. Checks would have been flying at me in the mail. 

[00:16:21] Mahan Tavakoli:
One of the things I really like about you and your story Deidre is that I believe you take energy from those comments and those experiences and funneled them into creating something even more successful, in this case Workboard, now you mentioned that it was the friction that you were experiencing at IBM, that led to the idea behind Workboard. What is Workboard and what is it that you provide your clients? 

[00:16:51] Deidre Paknad:
 So Workboard is a SAS company that helps organizations execute their strategy faster with the people in the teams that they have.

So that means get everyone aligned on the objectives, like what part of the strategy are we executing this quarter? OKR's if you will. So we're aligned on that and that flows into the business reviews and the ops reviews and the staff meetings and the cadence meetings, that we'd have both alignment and accountability and attention to those things that move us closer to strategy achievement, and we have the line of sight to that. We have the data on it. The question I was always being asked at IBM, where are you going? And how close are you? That should be widely transparent in organization. What the platform does is make it very easy for even the largest organizations, to get every team aligned on the strategy, and what we're trying to accomplish this quarter gives everyone transparency to that alignment and then flows that right into their ops reviews or business reviews or staff meetings in their one-on-ones. We call it a digital operating rhythm. 

[00:17:55] Mahan Tavakoli:
 That digital operating rhythm has helped a lot of organizations scale. In part, John Doerr popularized the concept, which is measure what matters book and that has done a lot of good in the conversation around OKR's in some of the conversations I have people discounted and say, well, that's for the Googles of the world or for the Amazons of the world. It doesn't apply to other organizations.But your experience at Workboared shows otherwise. 

[00:18:26] Deidre Paknad:
Workboard customers today include, Humana Anthem, AstraZeneca, Merck, Medtronic, Ford, Renaud, Bosch, Zed F, Allianz, it's companies in every sector. And of course it's also Toast and Avalara and Guild and the high flying, just public companies, And obviously I, started working on this problem quite a long time ago when I was first working on it.

 You're quite right. There was a lot of friction where companies outside of Google's and the west coast companies would say. Yeah, I don't really need to iterate faster on my strategy. My five-year plan, my one-year plan worked fine and people just do what we tell them to. We don't need to include them in this whole strategy thing.

 They just take direction and they didn't feel threatened. They didn't feel urgency. And they work in environments where iteration and innovation at speed were difference-makers for their financial performance. Now, fast forward to the last few years, three years in particular, the year before the pandemic and the two in the pandemic, they absolutely feel threatened that their complacency is actually their greatest risk that the disruption is coming from every direction, not the same competitors.

You go back to the old days, like a GE had the same competitors for two decades. And the only way one would pull ahead is if they bought somebody and everybody knew who was going to get bought, like nobody snuck up on you. That is not the case right now. And it hasn't been the case for like, well, since Amazon bought whole foods, it hasn't been the case.

 Now this like disruption actually erosion of your position in the market can come from any direction. And there's a much different sense of that in large organizations add on the pandemic and what we saw for the last eight quarters. Is it whatever you thought at the beginning of one quarter? Was no longer true a hundred days later. It was a surge, it was fires, social justice issues, is inflation. It was supply chain. Every hundred days, the entire climate of how your company was going to drive its strategy changed. And that need to iterate at a super high cadence, makes large companies just like grow startup companies where you're iterating constantly because you are learning constantly and you're trying to optimize constantly. It doesn't matter what kind of enterprise you are today, you better be iterating and learning constantly 

[00:20:46] Mahan Tavakoli:
 Deidre, one of the important things to underline is that while in some respects, that pandemic has accelerated some of that, these are changes that have been in place.

 I had a conversation with Azeem Azhar, he has a brilliant book, the exponential age, and talks about the exponential technologies that will significantly impact our lives and therefore organizations over the coming years. So, what you're talking about is that there is a need for speed and agility and that alignment for all kinds of organizations.

It's no longer that you can sit down and come up with a three-year strategic plan and check every year where you are in track towards achieving that. 

[00:21:32] Deidre Paknad:
That's right. I get it in my role, have a lot of conversations with leaders of all kinds of companies, including a bunch of the ones I mentioned. And there is a different sensation today that our plans, our long range plans, they are pure hypothesis.

 And not only are they pure hypothesis, but the assumptions upon which those hypotheses rest, those assumptions get proven and disproven incredibly fast right now. That speed of change in business cycles and technology cycles and customer expectations is pushing on those assumptions that underpin our strategy at record speed.

 You can't operate with a brittle mindset and over attachment to a precision plan for the long range. There's real shift to iterative business, right? The iterative pursuit of a vision versus the precision pursuit of a defined plan three years out from now, and there's just a different recognition of our inability to predict the future with any degree of accuracy. A CEO or president of a business, who I was in a conversation with and she called it like the delusion of omniscience. We used to think that we were omniscient and we could actually see what was going to happen three years from now. She can nearly just laugh at that whole thought.

 We can set direction and then we really actually need to dynamically iterate forward, and this is where I think platforms and the operating of the make an enormous difference. Two things come into play there. One is if the leadership team iterates on what the strategic priorities, what are the objectives and results we need to drive in the next quarter are, what we need to learn in the next quarter.

 If the leadership team does that, but nobody else knows, and nobody else comes along, the leadership team didn't really do that. You didn't really iterate. You just had a comvo, you just talked, nothing comes of the talk. And so this need to both iterate and mobilize people is a really big one. 

The second really big need is, if you don't have data about your execution faster, you can't make the decisions in the period to optimize, right? Everything is accelerating. And so I need to mobilize people faster and I need data for decisions on optimizing and de-risking on our achievement way faster so instead of a quarterly business review, I'm looking at it weekly. 

[00:23:53] Mahan Tavakoli:
 As you mentioned Deidre, it's important to have the data and that understanding and the communications.

 One of the challenges I see when I interact with clients and speak to leaders is that they believe that there is a lot greater alignment and focus in their teams and organizations than there truly is. Now even pre pandemic and remote work and hybrid work, they believe there was alignment when there wasn't, now there's even less alignment.

 What is your experience as you work with organizations on the alignment or focus that you see with respect to teams achieving that purpose of the organization? 

[00:24:35] Deidre Paknad:
 Truer words have not been said on the delusion of alignment. We started an OKR coaching professional service way back in 2016. And so over the whatever five, six years that that is, we have literally facilitated and coached thousands of teams, including executive teams on aligning on the objectives and results are trying to achieve in the year and in the quarter. And early days, I did a ton of this myself, student of leadership, student of strategy, obviously learning a lot about how to build a better business up for Workboard. We've never met a team that was actually aligned and of course they all believe they are and there's, we even have a sort of a readiness thing we do with them, which is alignment is messy work, and it's messy for a couple of reasons. And the first of which is it's really disappointing when we find out how misaligned we are. The good news is, as soon as we find that out, we can go on to becoming aligned. As soon as we find that out, it's the leader's job to get everybody aligned. Right? You don't, want to think you're not great but today, fast forward, any, it is much, much, much harder, not harder for the leadership team to get aligned with amongst themselves, which was always hard, that's still hard, it's still intellectually weighty work, super important, but weighty, it's harder to get everybody else aligned now because you are so much more dependent on the skillfulness of team leads the edges. And because Either the all digital or hybrid world in which we now must team, unless you have a mechanism to be very inclusive in that conversation, unless you're inclusive in the conversation you end up with the manager dictates the loudest voice drives what it is we decide to do.

 And it's very easy for half the people on the team to kind of sit out and not engage in determining what the impact that team will create in the quarter, not care about what that impact is, not even tuned into it. And when they don't care, as you're getting aligned, they definitely don't care as you're executing.

 And that need to include people in what it is we're trying to achieve at the team level and how that fits into the big company level. That need is not only harder in the pandemic, every single rent we work in a home distributed environment, it gets harder still, the fatigue overlay on the distributed teams world is a very real factor in how much energy people bring to the strategy you have. And if they don't bring energy to it, you don't get urgency for achievement. 

[00:27:04] Mahan Tavakoli:
This is something that is not going to get easier a month from now or a year from now, there is no turning to switch and going back, there was a lack of alignment, pre pandemic, but all that hybrid work has done and will continue doing is make the need for that alignment, transparency, communications, tracking the measures that matter even most important.

 So this Deidre, as you both lead Workboard yourself and interact with a lot of leaders that implement OKRs into organizations. What are the leadership capabilities you think are required both at the senior levels and throughout the organization. To make the organization aligned beyond and besides just the methodology of implementation of OKRs.

[00:27:55] Deidre Paknad:
I think of OKR is as a part of the operating rhythm, they're the mechanism for alignment, super important that we have a common language for aligning on value and OKRs give us that. They're a syntax and a structure so we all can actually speak the same dialect for agreeing on where we're going and what we're measuring.

 Agreeing on how much ambition we want in the direction we're heading. But just the way I think of it as alignment without accountability is all pain, no gain. It's hard to get aligned, but if you get aligned and then you actually just don't execute against it and you don't drive to that, like what a waste of, you know, emotional calories plus hours.

 Here's our part of that operating with them. They don't suffice for it. And so the first thing I would say for leadership required now, I think is this recognizing that the left brain, right brain of an organization is alignment and accountability. They must go together. And most big companies in particular, they have operating rhythm of ops reviews and business reviews and cadence calls, right?

 If all of that is happening and it is not about the OKRs we agreed on, then you really cannot get the body to function. You're driving one way after you agreed to drive another way. And that is super messy. So for leaders in particular thinking of left brain, right brain alignment, accountability, and thinking about how do I make sure that that's truly truely a whole brain is I think super important. The next big one required now I'd think is iteration as the primary mechanism you think of for moving the organization forward, where there's a huge premium right now, and iterate to learn, iterate, to learn, iterate, to learn. And lots of leaders, big enterprise in particular, have a history of measuring to reward, not measuring to learn.

 And if you're transforming your business while many are you're transforming your business model, you're trying to become SAS company, when you used to be a automobile maker, there's a lot you don't know, and you don't know what that is that you don't know, and you need to be iterative and learning and build that into the genetic fabric of the company.

And the way that starts is how leaders show up themselves. And so there's of the kind of phrases we use is get really good at leaning into the red and asking the question, so what are we learning? Not what the hell went wrong here, What is this teaching us? and leaning into the red, as opposed to hunting it down, that starts at the top.

 Like how leaders show up is either giving everyone permission to learn and permission for ambition or giving everyone, the direction that you should aim for safety, there'll be no learning here. You better be darn sure about what you put out there and deliver exactly that. And since very few people can predict the future, what people start putting out their shrinks right at the moment in time when actually elevating people, raising ambition, raising the learning cadence, raising the iteration heartbeat of an organization are important, your traditional management behaviors start shrinking people back into safety mode. And I think that can be a super fatal spiral, actually. 

[00:30:51] Mahan Tavakoli:
It is also scary for a lot of leaders in organizations. That's one of the reasons at times, They discounted and they say, well, this can be an entrepreneurial mindset or what they call a Silicon valley mindset, but in our organization.

 And then they come up with the reasons and excuses for not iterating, not taking those chances, but part of what you are saying and is that for all kinds of organizations, It will require that kind of leadership with iteration, with the learning, in order for the organization to be able to thrive and grow. 

[00:31:30] Deidre Paknad:
 Absolutely. The climate in which we live now, all of our businesses require all of us to behave with a bit more startup mindset and I call it actually, there's seven flavors of OKRs and we have our own, which we call outcome mindset methodology, and it's particularly optimized to how do we help large enterprises given where they're starting meeting them, where they are, how do we help them unlock the power and if you will, the growth acceleration that OKR can provide, but don't automatically provide. But what I'm seeing in 2021 and 2022 is there's just a massive shift in how leaders feel about this topic. I used to hear all the time. Yeah. Okay. We're not that kind of. I never hear that. Right. It's very different.

Instead, I hear leaders saying I've got a culture of complacency and I need a culture of ambition, how can you help me? I mean, they've had the same hard year that everyone else has. And oddly, right. I think in some ways, great leaders of great enterprises are mobilized and energized in let's call it war time, where there's a renewed purpose and a renewed energy for leading the way forward into new territory.

 And if you are a leader, that's kind of more interesting than leading optimization of a cash cow. Like you get to like use your whole body, your whole brain in that. And I'm seeing invigorated motivated leaders who are excited about the change and transformation and leading the way forward into the next generation for their enterprise.

[00:32:56] Mahan Tavakoli:
This has been a wake up call for a lot of organizations and a lot of leaders, as long as I want to underline that for many of the leaders that I interact with, they believe that this is something that their teams need to take on and behave differently and be more open and part of what you've said, and I love about your leadership Deidre, is that the leader sets the tone through her behaviors and his behaviors, it's not necessarily something that they move down the organization for others to do things differently. 

Now, over the past couple of years, daydream, we've also been through a massive disruption with COVID and the pandemic. How have you, as a CEO of an organization, a startup on a fast track, been able to guide your organization forward? 

[00:33:47] Deidre Paknad:
Great question. It's well one quarter at a time is the answer. And of course we align on OKRs every quarter and we have radical transparency across the organization.

We had a strong muscle, frankly, for that. It's very easy for any new hire. Who's never met anybody in person to immediately know where their team is going, how that fits into where their group is going, how that fits into it. Companies going super transparent and not just transparent but clear like clarity and transparency together, make it easier for people to join your mission.

 In that timeframe, we tripled head count in the last 15 months. And obviously we did that without doing in-person interviews and so on. And that clarity plus transparency is like super important in this world, this dynamic. The first year of a pandemic, my approach personally was, actually to put a big old safety net around every person at Workboard and their family, and that safety net add a bunch of layers to it, but it was very, very personal and very compassion centered.

It was kind of the best of times in the worst of times in so many ways, but you know, that first year, heavy west coast presence, both in California, Portland, and Seattle. And so like everybody home, the mix of Seattle and San Francisco being kind of epicenter. The social justice stuff. And then the fires, which were also all up and down the west coast, which, we evacuated people in multiple places.

 The safety net was we had food boxes on hand that when somebody was sick and who might be living alone, who had to be isolated, the food box would drop in a day, get a food service lined up and wired. Every household got flowers every single week of 2020 to bring a little bit of brightness and joy in just a tiny bit.

 We had this whole sort of call down network, which was, who needs help when somebody who just owned the mental health and safety of people in the team. particularly in that first year, we paid special attention to people who took care of the parents. Special attention to people at small kids, special attention that people lived alone.

 We had just a whole host of programs around. Which were literally safety net. The graduation, everybody knew everybody's kids. We had a whole graduation ceremony that had kindergarteners and post-docs and all those, they all knew each other and everybody attended. And it was just really, we called it a village.

 And my job was just to put that safety net around everyone that year and make sure we get all thrive and be successful in the bonds created, then our permit. 

[00:36:18] Mahan Tavakoli:
 For organizations to thrive, they need to have leaders with your humanity Deidre, that place the individuals in the organization first, not just with respect to statements.

 One of the things I say a lot is the fact that many leaders have learned the right things to say with respect to the importance of people, importance of empathy, compassion. However, the behaviors, sometimes aren't aligned with those. What you have done over the past couple of years is make sure that what the organization actually does for the people, shows them that true care, that true compassion that is important for the organization to feel a sense of belonging and for the team members to want to contribute, to achieving the purpose of Workboard. 

[00:37:08] Deidre Paknad:
I think what gets hard and particularly in super scale and in tough situations, right. Is you can want to show up one way and there's, you may not have the capacity for your company to live up to how you'd like it to show up.

 And that I think for a lot of leaders is, unfortunate, right? Where their intention is genuinely good. But their capacity to execute on that attention as their job gets more complex. That often is where the gap is. And I, to go back to the humanity thing, I total Pollyanna, right? So I assume Goodwill always.

 And I assume that people are every single day just trying to do their best, be the best version of themselves. And one of our core values is humble expert. And the expert thing is a clear expectation that you show up the best in your job. But the humble is to recognize that that's a lifelong pursuit, not when you were already there. And to be humble enough to recognize that your coworkers are also in that lifelong journey, not there and that they're learning every day, maybe even every hour, how to be a better version of themselves and be generous enough to allow that to be true.

 And I think that's super important. So when I see like gaps between what leaders say and what they do, I open up the generosity there to say, I bet they know that, I bet they're working on that. And I bet they don't love how fast they're working on that either. And then okay, how can I create space?

Or even from Workboard's perspective, how can I be a part of the inclusive, forward-leaning, iterative, culture forward organization they're trying to build, right? Like how do we help. It's a no indictment policy. 

[00:38:41] Mahan Tavakoli:
What a beautiful way to extend that grace to the leaders who themselves are working and need to continue working on themselves.

 Now, as you were dealing with this pandemic, I know you as a CEO, experienced a big loss in your life, losing your sister, how were you able to manage everything you had going as a CEO of Workboard, going through such tough times. 

[00:39:12] Deidre Paknad:
I have no idea how I did that. I'm hoping I can do it twice. you know, we went to work from home on March 7th and two weeks later, a lifelong friend of 30 years, maybe I've spent 25 new year's Eves with her was diagnosed with brain cancer and she passed in July. My sister was diagnosed two weeks later with cancer, that by November had also spread to her brain and she passed away in December and it was tough. It was ridiculously hard. That was all happening at the same time, I was trying to manage that safety net I just described, and try and make sure that everybody, the whole extended village was okay. And there are a lot of people were not okay, including, not just my family, but in other people's families. And then I got good at compartmentalization. From March until November I, did a decent job of holding what was happening to these people that I loved holding that in one place and then doing what needed to be done in the company and another, including the period where I had my go bag pack because my house was on the evacuation line for the fire.

 It was pretty wild year. My business doubled that year. So nothing was easy. And I did a decent job of compartmentalizing until the very kind of tail end of my sister's life. I think I operated on the entire time thinking if I just used enough willpower, which obviously has gotten me fairly far in my life, she can out run this thing. And I put a lot of energy into willpower during her and me and she wanted to run and she, was not ready to quit. And so that was okay until it was clear, we were going to lose and then it got really hard. Then I could not pull up the compartmentalizing.

It was just, it was very, very difficult. And that was like Delta surge. It also happened to coincide with a huge and very distracting approach by a big company to acquire Workboard, which required my attention and also required secrecy and the comment they weren't exactly exactly at the same time, like, the same date.

 And that was hard. I could not easily do all the jobs I had at the time. And what became kind of clear and was clear actually, even for six months after, is how extraordinarily expensive it is for the CEO to have a life because you get to a point where you really cannot cover all those bases. Well, and my personal situation took a huge toll on my ability to be a good CEO during the day.

 And that toll shows up, a quarter later in the way the company is functioning. And because I didn't want to make my grief and my loss public, and inside the company there I'm sure plenty of people who thought what was wrong with her, why don't we do it this way? Why didn't we do that? How come this isn't fixed?

And, the answer is, I just simply didn't have the capacity to get there. It's tough for CEOs with personal, significant personal challenges at the same time as significant business challenges, there's like a no slack, no leeway. That's pretty tough like when they say it's a lonely job, they have no idea how lonely it is. 

[00:42:07] Mahan Tavakoli:
It is incredible. The fact that what you had mentioned earlier, Deidre is the importance of us extending grace and how all people in all positions, all states of life need that grace extended. We don't always know what's going on in their lives, so that humanity, that grace is really important as we want to bring out the best in people as we want to lead with the humanity that you've done so beautifully with Workboard. 

Now, as you lead the organization forward, a lot of the client are struggling with the future of work, both the hybrid elements of it, and how to get their teams to collaborate and work effectively would love to know some of your thoughts, both with respect to maybe what you're planning at Workboared And just what you tell your clients in addition to the implementation of OKRs in addition to the humanity and authenticity with which you guide leaders to lead their teams and organizations, what else should leaders consider for the future of work. 

[00:43:19] Deidre Paknad:
I think that things had become important in, some instances are really new things. Like things we couldn't have conceived of and even simple stuff. You're right. OKRs help because a team amongst itself knows what it's trying to accomplish, which affords the members of the team the autonomy to work at their house towards common team goals and common team outcomes. And the team knows how that fits into the context of the group and of the company where there is a shift and a future work world is when teams were in-person and they sat around a room and they brainstormed on what their objectives are, what their intention really is and what are the results or the real outcomes they think are great in the quarter, when they're in the same room, having that conversation, you have a much higher probability that everyone's brain power is in the conversation, have a higher probability of inclusion in an in-person setting, move to zoom, move to teams, and you have very low probability of true inclusion of everyone's brain power and willpower, which we all know skill and will are pretty important parts of achieving what we want. You have a pretty low probability. If somebody opens up a Google doc and starts writing, the manager starts dictating what the O's and the KRs are going to be meaning, team. Here's what we should do. And here's the results we should measure. And then you have people sitting on the phone and like, okay, whatever you say. And you've got maybe some loud voices who dominate what the team should do, and then you've got everybody else who's abdicated, passive doing something else, stopped caring a quarter ago. That dynamic with an even a single team, much less a thousand teams in a 10,000 person company, that dynamic is incredible drag on the potential of an organization, incredible drag. Like you hire people, so they'll bring their brainpower to work. And if you can't bring it even into the objectives and results conversation, you're not bringing it into the execution either. And that we're changing entirely the experience that we provide to teams on how they said OKRs a really white boarding canvas experience, coaching in guidance on how to have an inclusive conversation. 

The new conversation starts with silence as opposed to, it starts with a lot of talking and shifting the way we create that collaborative experience to reflect the fact that some of us are in the room, some of us are not in the room, and inclusion of intellectual horsepower is super important to the organization's strategy, its achievement, and to its potential ambitions. That's a big change to me. And it's even our coaching methodology is shifting to say like even the practice, like recognizing how it took place in a physical world, can't just be straight across to the virtual world. It cannot be. 

I think of that opportunity and we're work boards out with the platform is actually we need to democratize the opportunity for achievement in organizations, and we need to accelerate how we go about that and that democratized to the edges, the potential for impact and potential for outcomes in the organization's context and that's a change in mindset, change of behavior, a change in the platforms we use to help people get there. It is not chat. That is not the answer to future. 

More noise is not more achievement, it's more exhaustion. I actually think there's a point where chat, whether that's on teams, where that's on slack, it starts to become the Instagram of adults, all those things we talk about kids and Instagram addiction and the distraction and the cost to mental health and to purposefulness. I think we have a version emerging that is team slash slack at work for adults. And I think there's going to be a swing away from that to quieter spaces, room for thoughtfulness room for thinking both individually and thinking as a team, I think that's going to look very different than anything we've seen before.


[00:47:13] Mahan Tavakoli:
Deidre, it requires for us to design new ways of interacting with each other. New ways of collaborating with each other, rather than trying to bring things from the past or even from the virtual world and shove them into the future. Taking a design thinking approach, had a conversation with Sarah Stein Greenberg who heads up the school at Stanford, and she talks beautifully about, we need to redesign the conversations, redesigned the collaboration, so that's the great part of what we need to do. 

Now you've done that beautifully at Work board. You're going to continue doing that. What to see, are there any leadership resources or practices, Deidre that you typically find yourself recommending? 

[00:48:02] Deidre Paknad:
For Me, one binary, which is exercise every morning. If you mess that up, it's I do mess it up. Oh, okay. Does it matter? It actually matters every day is binary. Someday, hopefully I'll actually, you know, truly, truly understand them, but that one's particularly important I think where resilience and iteration are needed from you every day and where you get surprised incredibly often by external events, I think the durability that comes from starting the day with exercising or meditation or some movement, I think is a lifesaver really, and an enabler for leaders. I think I myself tried to practice the hypothesis for the future rather than I'm so attached to my plan that if it doesn't come true, I'll be devastated.

Instead it's on my hypothesis about what will be true two years from now, it's this right? And that's premised on these things and they might change. They just didn't actually make sure that my thinking isn't rigid and my attachment isn't rigid, but that I operate in a more iterative and fluid way myself, that might be a little bit like founders might be pretty natively like that in the first place. So that might be easier journey for me then than it is for others. And then. I feel quite strongly about how do I help the organization aim for greatness, not aim for safety. And when I say improve safety there, I mean, aiming at targets that are more about helping us look good than actually be good. And so how do I make it safe and energizing to reach for our highest outcomes where nobody's fearing that so they can get hung out to dry, but instead is actually motivated to see how far we can go. And that requires like almost constant thoughtfulness, which I am not perfect at, but I show up every day and try and be a little better at it and how do I help the organization unlock its fullest potential. 

[00:49:57] Mahan Tavakoli:
That beautifully captures what the leaders should do in leading their team to a vision of the future. First, the leader grounding themselves as you do with exercise, and then as Daniel Conaman also says viewing everything as a hypothesis. And then testing that hypothesis.

 You also have a joy and fun, as you mentioned of exercise. What is this with you doing cartwheels into the pool Deidre, and then your board of directors take extra insurance on you when you do that. 

[00:50:31] Deidre Paknad:
 I love doing cartwheels. I grew up with three brothers and I'm like super tomboy person. I water ski in pond with alligators in it, and I like to jump off the gangs and climb and dive and whatever I grew up outside and I'm still outside but doing cartwheels is actually especially into the pool, your head has to be in the moment and then you cannot take yourself seriously. And then there's this really big payback or pay off when you actually landed.

 It's like a microcosm of what perfect is, right? Like I'm fully absorbed in this moment living in it, and I'm not over attached to myself or my thoughts and it's very satisfying. I can do that all day long. 

[00:51:10] Mahan Tavakoli:
Deidre Paknad what a joyous conversation, both talking about some of the fun side and highs and some of the authenticity and the vulnerability and the lows, the systems and approaches, including most especially objectives and key results and to attitude of humanity and authenticity of leaders as they lead their organizations forward.

 Thank you so much for joining me in this conversation for partnering leadership Deidre Paknad 

[00:51:41] Deidre Paknad:
Thank you. Privilege is all mine.