娇色导航

It seems every week I鈥檓 on the phone with a 娇色导航or other technology executive who鈥檚 either contemplating, on the verge of, or has recently gone through the process of retiring. Most struggle with it. They鈥檝e been so heads-down doing the work that they鈥檝e failed to properly and intentionally prepare themselves for this next chapter.听

On a recent episode of , I sat down with two former technology executives who鈥檝e transitioned to 鈥淐hapter 2鈥� in their career journeys with the same success and dexterity they demonstrated in their operational roles. Diana McKenzie was 娇色导航at Amgen, Workday鈥檚 first CIO, and held numerous roles at Eli Lilly.听Karenann Terrell served as an executive at big brands like Baxter, Walmart, and GSK.听Today, they鈥檙e both involved with a range of executive advisory and board roles, from public and private board memberships and private equity work, to investing, continuous learning, philanthropy, and more. 听

During the podcast, they shared advice on preparing and navigating the process to fulfill a new chapter in professional and personal life. Afterward, we talked about their lessons learned once the dust settled. What follows is that conversation, edited for length and clarity.

Dan Roberts: I find that those who thrive in the next chapter of their career journeys gain new perspectives through these experiences. In that spirit, if you knew then what you know now, what would you have done differently when you were in the CxO chair?

Diana McKenzie: I鈥檝e learned much in this next chapter. If I had to call out one thing, I would鈥檝e struck a better balance of 鈥榠nside-out鈥� focus on delivering outcomes that mattered to our CEO and the company with an increased 鈥榦utside-in鈥� appreciation for the way in which the company鈥檚 external stakeholders valued those outcomes.

Through the lens of serving on boards and advising startups, I鈥檝e developed a more informed appreciation of, and greater empathy for, the challenges CEOs must navigate with a broad base of external stakeholders, including shareholders and analysts. For instance, I wish I listened as intently to understand the 鈥榳hy鈥� behind the analysts鈥� questions as I did our earnings presentation. I would鈥檝e prioritized time to read the post-earnings analyst reports to round out my perspective of how our performance was being valued. I likely would鈥檝e made different choices about how I supported the CEO and guided my team.

Digital leaders who effectively balance these two perspectives have the potential to play a far more valuable role in delivering the right business outcomes, supporting their CEOs and executive teams, and driving long-term value for shareholders.

Karenann Terrell: I was running very large responsibilities in very large companies, mostly multinationals, and I didn鈥檛 really recognize or understand how much my productivity and optimization was important to the results that were going to come from my job. So I wasn鈥檛 careful about surrounding myself with a support system that lifted and optimized me in a way that could lift and optimize the other parts of the organization I ran. I just moved along saying I鈥檓 going to optimize myself. Well, when you get to a chief level, it鈥檚 very important you set things up so you鈥檙e the best for all the people who work for you, and that you鈥檙e the best in leading the function. I can see that more clearly now, looking back and through companies as advisors or on the board, than I could ever see while I was on the operating side of the business. So I would do that differently. I鈥檇 set up my world in order to make sure that everything I鈥檓 being asked to do is at an optimal level.

What鈥檚 also been eye-opening for somebody who values how the ecosystem works is seeing how driving speed and transformation in technology and innovation comes from companies that are highly motivated through investors 鈥� whether they鈥檙e giant investors, angel investors, or bootstrap investments. I was blind as to how to get that ecosystem player to work with others because I didn鈥檛 understand the daily pressures, where I could look at their forums and say, 鈥極h, they seem to have four people from the same investor. That鈥檚 interesting.鈥� In the pressures to get what I needed from those companies while I was an operator, I had no idea what that actually meant. I think if I had better known how the investor world worked, with venture capital and privately invested companies with whom we worked, I would鈥檝e behaved differently.

Karenann, you鈥檝e pointed out that when the C-level leader ultimately makes the decision to hang up their operational boots, it isn鈥檛 always an easy one, and the process itself can feel challenging. Can you talk about why that is?

Terrell: I think one of the fears that CIOs have with their decision to go into retirement is that they鈥檙e not going to be fully there. Once you say this is my last job, you start to lift the control of when that happens and who decides who鈥檚 going into the seat. By the very nature of that, you start to lose your power.

People feel they鈥檝e become lame ducks, or not a part of the process, or the timing doesn鈥檛 fit theirs. So they want to keep those decisions as quiet and hidden as possible, when we have no experience in doing that, because you鈥檝e either been at the same company your entire life 鈥� rare among CIOs 鈥� or you鈥檝e moved from place to place. Nobody really teaches you what to do when you retire.

When it comes to the next phase, what if someone hasn鈥檛 built the big brand of a Diana McKenzie or a Karenann Terrell? What鈥檚 the right pathway for them?听

McKenzie: There are likely many paths tech leaders can take if they haven鈥檛 benefitted from building a branded portfolio as an operator. One path I often promote is for these leaders to consider private equity and VC advisory as a steppingstone.

If a top tech leader is considering their pivot to a portfolio chapter with public board roles, and is unsure how to make that happen, they could begin by reaching out to the PE/VC community with whom they鈥檝e developed relationships throughout their years as an operator. These firms offer various opportunities to engage, ranging from advising portfolio companies to advising the PE/VC group at the portfolio level, or serving in the capacity of an operating partner. Advisory roles can lead to a board role with the portfolio company and an opportunity to aid the leadership team with the process of preparing for an IPO. This in turn offers the ability to stay with that company post-IPO, serving in the capacity of a public board director.听

Choosing this path requires developing robust relationships with the VC/PE community while in your operating role, ideally three to five years before your planned pivot. This not only contributes to making you a higher performing tech CxO, but it also paves the path toward extending your personal network with other C-level leaders in tech, which becomes a valuable asset when transitioning to your next chapter.

Terrell: Most of the people asking this are either on a private or public board, and the first place you start to understand what board-level opportunities might be out there is with your own board members. There are very easy entry points. You can say, 鈥業 noticed you鈥檙e an advisor to KKR or I noticed you鈥檙e on this board. Could I get 20 minutes of your time one day to talk to you about it?鈥�

There鈥檚 nothing a board member likes more than somebody from the management team saying, 鈥業 noticed you鈥檙e on that Indian unicorn company that鈥檚 going public in India. I have some questions about that whole thing.鈥� When somebody knows what I鈥檓 working on, I say, 鈥楬ey, let me tell you what I know about that. Is there anybody you want to meet?鈥� I can鈥檛 think of board members who don鈥檛 act like that.

And that鈥檚 a built-in future network for you. Either you鈥檙e on a private board with other board members who are invested in trying to help you out and are looking for good talent they can recommend the next time a board seat opens somewhere, or they want to tell you what they want to know. It鈥檚 about finding birds-of-a-feather opportunities. That鈥檚 how I did it. It鈥檚 very hard to figure it out if you鈥檙e not actually leveraging your existing relationships. This is one of the huge power opportunities in the women鈥檚 IT leadership organization, .

So I always say to people, 鈥楪ive your assistant a little project: Go map everyone on your board, or everyone who鈥檚 been on your board, and what boards they鈥檙e on.鈥� Since it鈥檚 all public information, it鈥檚 an easy thing to do, and that鈥檚 how you drive your network and your influence.

McKenzie: If I recall recent research correctly, approximately 60 to 70% of all public board positions are filled through personal networks. Boards often look to existing board members to identify a slate of potential candidates before engaging an executive search firm. When I鈥檓 approached by fellow board members or acquaintances in my network to recommend prospective board candidates, I turn back to my network to find potential connections I can make. As Karenann referenced earlier, this is just one example of the power of participating in a community like T200.

One of the mystery questions we didn鈥檛 get to during the podcast was from Sue-Jean Lin, 娇色导航of Alcon, about recent research showing how a digital-savvy board creates enterprise value. She wonders whether digital is driving the performance, or is a digital-savvy board more open to innovation, and therefore creating more value?

Terrell: Peter Weill is another one doing research on this topic, because beyond digital, it moves to real-time enterprises. Digitally inclined businesses don鈥檛 necessarily have digitally inclined boards. One doesn鈥檛 equal the other. A digital board asks questions that are directly connected to physical and digital integration. Without a digitally minded board, you find those topics being discussed in silos as opposed to an integrated part of the business. That鈥檚 why I believe digital natives are massively valuable on boards that are trying to make omni-related moves. Otherwise, you just get separate solutions. You get an 鈥榓nd鈥� instead of a 鈥榩lus.鈥�

Along those same lines, Deloitte studied corporate 10Ks and found that companies that talked about their digital strategy, tech bets, and change strategy had a 14% higher market cap than those that only talked about their digital strategy and tech bets without discussing how they鈥檙e going to lead the change. What鈥檚 the board perspective on that?

Terrell: It used to be 鈥榙igital as a differentiator鈥� in market value. Now, non-digital is going to be a failure mode for companies. Whole companies are going to just fail and fall out, and what鈥檚 being discussed in boards is that we鈥檝e got to finish our digital transformation because AI is the frontier around which we鈥檙e going to have to drive productivity, product integration, or whatever it is. And so digital transformation has got to come with the topic of change management and adoption.

McKenzie: If you鈥檙e interviewing for a board seat and you鈥檙e not sensing a discernable 鈥榯one from the top鈥� with respect to how technology or digital is being embraced as core to the strategy, you may want reconsider if that board opportunity is for you. To compete successfully in today鈥檚 macroeconomic environment, board members, CEOs, and their executive teams need to demonstrate a commitment to making technology an integral element of their strategy, along with a willingness to invest in the operating model, incentive system, and talent changes required to successfully pivot. Prospective board members may even consider making this a filtering factor for all incoming board opportunities when conducting their board search.

Let鈥檚 wrap it up with the big question: How do you manage the great balancing act in Chapter 2, because it seems like you could easily get sucked back into 80-hour weeks.

Terrell: I fail some weeks.

McKenzie: Me too!

Terrell: Because who we are that made us successful in our operating careers are people who put our whole self in. Why would we think we鈥檙e going to suddenly become, 鈥業鈥檒l just dabble a little bit鈥� people? The thing about portfolio life, though, is you have the ability to push and pull things that have far less permanence and commitment. You have the choice to pick and choose, come in and out. Sometimes the things you鈥檙e involved in all get hot at the same time, but you just plan accordingly.

McKenzie: I will admit saying 鈥渘o鈥� was not my strength when operating. Post-pivot, I鈥檝e gotten better at it, despite what my husband might tell you. I find I sometimes have to say no or 鈥渘ot now鈥� to cool stuff, but it鈥檚 because I have enough cool stuff already on my plate.

Terrell: Why is it thought that when you go to a post-operating career, you鈥檙e now a sole proprietor? I have an assistant and a research assistant. I don鈥檛 have to be out there all by myself trying to figure it out. I鈥檓 a multi-million-dollar operation, and no multi-million-dollar operation I know runs with just the founder.

McKenzie: Serving as a technology advisor is a great way to invest in continuing education. Plus, I鈥檝e been fortunate to curate a discrete set of diverse communities offering valuable continuing education perspectives on subjects inclusive of emerging technologies, business strategy, the future of work, and corporate governance 颅鈥� all critical to remaining relevant as a board member and technology advisor.

For more pragmatic and actionable advice on how to prepare for that next chapter, tune in to .