Decide who is deciding. Groups and committees are really bad at decision-making, so you should understand who is going to make a decision, recognize who might need to be told (so they can overrule the decision), and who needs to collaborate. But if you don’t have an actual decision-maker, you’ll end up with a lot of finger-pointing when the non-decision results in a bad outcome.
As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Andy Ellis.
Andy Ellis is a visionary technology and business executive with deep expertise in security, managing risk, and leading an inclusive culture. A graduate of MIT and former US Air Force officer, Andy designed, built, and brought to market many of Akamai’s security products, leading the Fortune 1000 company from its start as a content delivery network into an industry powerhouse with a billion-dollar dedicated cybersecurity business. In his twenty-year tenure, Andy led Akamai’s information security team from a single individual to a 90+ person team, over 40% of whom were women. In running Akamai’s security program, Andy designed systems, governed risk management, implemented policy, and supported go-to-market functions. Widely respected across the cybersecurity industry for his pragmatic approach to aligning security and business needs, Andy regularly speaks and writes on cybersecurity, leadership, diversity & inclusion, and decision-making and is the author of the book, 1% Leadership: Master the Small, Daily Improvements that Set Great Leaders Apart.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
I’m Andy Ellis. I was kicked out of MIT for playing too many games (and not attending classes). I wandered for four years, picking up the Spirit of Disneyland Award while giving cast members clean clothes, and the Wine Spectator’s Award of Excellence while curating a small inn’s wine cellar. I realized I should finish my education, and managed to return to MIT on an Air Force ROTC scholarship. I spent a few years in Sumter, South Carolina, learning what’s now called cybersecurity, and then spent two decades working my way up at Akamai from the first security hire all the way to becoming the Chief Security Officer, with four patents to my name. I was inducted into the CSO Hall of Fame in 2021.
Along the way, I built one of the most inclusive work environments to be found in cybersecurity. In the 15 months before I left, I had zero turnover, and a team that was 40% women. The lessons I learned on leadership are collected into 1% Leadership. It’s a leadership guide for aspiring and veteran leaders that focuses on mastering the skills of leadership, rather than the form of leadership. I don’t pretend there is a single epiphany moment — just lead like this and you’ll be a great leader — rather, it’s the small moments of leadership that combine to build amazing leaders.
Since then, I’ve been working in the early stage cybersecurity world: I’m an Operating Partner at YL Ventures, which invests in seed stage cybersecurity companies; I’m the Advisory CISO at Orca Security, and I have my own cybersecurity and leadership consulting practice at Duha.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
Only one? That’s a hard ask — almost everyone I’ve interacted with across my career has helped me along the way (even if only by providing a counterexample). Every time I get asked this question, I like to identify a different person, so today I’m going to express my gratitude to my book agent, Jeff Shreve, and not just for getting me a book deal. Writing a book is a difficult endeavor, but I’m pretty sure that managing an author is even harder — Jeff was often the first person outside my house who read some of my chapters, and he’d have the hard job of (delicately) telling me which ones needed a little polishing, and which ones were utter turds. The grace and humility that he brought to that process was eye-opening for me, and helped improve my own leadership skills.
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
When you’re an executive, you often have insight into the chaos that swirls inside an organization. Maybe you can see an impending layoff coming, or you can predict a material change or reorganization that will be happening, but you can’t yet tell your team. There are two common traps that leaders fall into. One is to shut down, ceasing communication with their team, so that they don’t accidentally leak information; this leaves their team surprised and shocked when the change blindsides them. On the flip side, some leaders expose their team to the chaos and uncertainty, increasing their stress, especially if the big change doesn’t happen.
Navigating between those two is always a challenge, and I’ve had to do it multiple times. One that stands out was when we’d been asked to do a new project that would require incremental headcount — but we weren’t going to get any. There were hard trade-offs to be made, and all of our managers would be affected, no matter what we did. So we paired up all of the managers, and asked them each to propose an option for how to proceed. While they all did good work, none of them reached a workable solution — one team even explicitly said it was an impossible challenge, and they’d prefer that we just made the decision.
Ultimately, I and my direct reports made that decision, but by exposing our managers to just enough of the problem, we’d minimized the stress and confusion that would’ve made implementing our team restructuring even harder.
Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?
More often than I can recall. The hardest part of leadership isn’t exercising your authority — that’s easy to do — it’s finding the paths that others aren’t willing to take, and taking them, to make the world a better place behind you. That’s what motivates me — knowing that when I spend the extra time finding a way to support one member of my team, that everyone around now has a playbook that they can follow to do the same thing.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
Oh, difficult decisions between two good paths? Sign me up for more of those! Most difficult leadership challenges are when you have to decide between two bad paths, usually one of which is low-friction, and one of which is high-friction.
When my leadership team first added distributed staff in a new location, long before Covid, we started to discover that the non-HQ team was feeling isolated and confused. We’d discuss a topic in the staff meeting, without resolving it. As the meeting broke up, we’d disconnect the video, and continue the conversation with the HQ team. We’d come to a conclusion, and move forward, often forgetting to even circle back to our colleagues.
We wrestled long and hard with how to deal with this — after all, we got a lot done in that walk back to our desks, but ultimately, I went with the hard choice to stop talking as soon as the meeting was over. We enforced a discipline on ourselves, and while it was expensive in the short run, it gave us motivation to fix a number of other challenges with how we ran the team.
It sounds like a really small decision — and it was — but it changed our culture in so many ways going forward.
What process or toolset can a leader use to make a choice between two difficult paths?
The single most important set of tools for a leader is a set of core values. I don’t mean the pablum like “Excellence” or “Integrity” that most organizations use; you should have hard values that you get wrong on a regular basis, and you want to get more right as you go forward. As you look at difficult paths, test them against your values — if you don’t like the compromises you’ll have to make, maybe that path isn’t the right one for you.
You decide on your values by examining the decisions you regret: what do you wish you had done at the time? What value did you not actually value? By exploring who you wish you had been in the past, you can set up road signs for your future.
Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?
I think the idea of a single mentor is now more the exception rather than the rule, as people move through their career in so many different places; instead, people should build out a “mentor network.” Since you aren’t relying on a single individual who will always have the right advice — a framing that almost necessitates a mentor who is senior to you — you can build your network by including peers and juniors who are specialists in areas you need help in. This also makes the relationship more bilateral, as each of you likely can provide guidance that the other will appreciate.
What would you say is the most critical role of a leader when faced with a difficult decision?
Owning it. Whatever decision you ultimately make, it belongs to you, and you can’t blame someone else for it.
Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?
All the time! One of my favorite chapters in 1% Leadership is titled “Regret is an act of forgiveness to your past self.” If you never regret a choice, you can’t learn from your own mistakes — but like with forgiveness granted to others, you also need to move on once you’ve learned the lesson and not stew in the possibilities of what-might-have-been.
What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate and engage their team during uncertain times?
Address the needs of the people in your team. People want to do valuable work — so make sure they are doing valuable work, that they aren’t wasting their time, and that they are appreciated.
Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?
Analysis paralysis certainly tops this list: don’t put off making a decision for too long. The reality is that you’ve already made the decision, and you’re just using analysis as cover for your choice; delaying the decision isn’t going to make it any easier.
Secondly, listen to your team for their feedback. While they might not have all of the information that you do, simply discarding their input because you don’t believe what they’re telling you? That’s almost certain to run you into failure.
Finally, recognize that it is a hard decision. Don’t try to minimize the difficulties in the decision making process, or downplay the costs of your decision.
Based on your experience and success, what are the five most important things a leader should do when making difficult decisions?
1 Understand your unacceptable outcomes. Certain choices are probably off the table for one reason or another, so you should identify each of those quickly, explicitly acknowledge them, and move on. But when you don’t identify them, you might spend a lot of time planning to do something that, ultimately, your organization will prevent you from doing.
2. Decide who is deciding. Groups and committees are really bad at decision-making, so you should understand who is going to make a decision, recognize who might need to be told (so they can overrule the decision), and who needs to collaborate. But if you don’t have an actual decision-maker, you’ll end up with a lot of finger-pointing when the non-decision results in a bad outcome.
3. Plan for change management. Hard decisions often need tight communication, and almost always need a transition path to get from the old way to the new way. Whether you’re affecting employees, customers, or other stakeholders, you rarely get to wave a magic wand and instantly implement your choices.
4. Plan for your downside. You can’t just assume that everything will go smoothly, so plan for how you’ll deal with the inevitable bumps in the road. Your hard decisions get harder in the future when people can’t trust that you can execute them.
5. Celebrate your allies. Rarely are you the only one who has to do hard work on your decisions? Publicly celebrate the allies without whom it wouldn’t have been possible so that they’ll be more likely to take this journey again.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Inclusion is reducing the energy cost people pay just to exist in a space. As a leader, you’re often pulled in a lot of directions by people with different agendas about how you should solve problems in the workplace (or society). By staying focused on our real goal as organizational leaders — reducing the wasted energy in our team — we not only have a touchstone for doing the right thing in any given circumstance, but we’re aligning what our employers hire us to do (improve output) with what our humanity calls us to do (be better to others).
How can our readers further follow your work?
You can read my book, 1% Leadership, wherever you find your books (physical, electronic, or audio)
My newsletter (https://duhaone.substack.com)
My Twitter or LinkedIn feed (@csoandy on both of those);
Or have me come speak to your organization!
Thank you so much for sharing these important insights. We wish you continued success and good health!
Author Andy Ellis On How Leaders Make Difficult Decisions was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.