I recently went one-on-one with Darryl Kelly, CEO of Aspect Software.
Adam: How can leaders hold themselves accountable?
Darryl: You’re going right into the hard questions, the hard truths. I love that. I love that there’s no holding back. And I think that’s what I’ve appreciated about your show and why I was so interested in having a conversation with you. It’s because you create this space for leaders to authentically show up and wrestle with what they’re wrestling with, and then there just happens to be an audience on the other side of that. So here we are, right in it.
I’ve been thinking a lot about leadership accountability. I think we should be transparent. I think you planted just a very brief seed, the smallest seed initially, when we were discussing what we might want to talk about, just so people can get a little behind the scenes. None of this is perfectly scripted. There’s a sense of authenticity in these conversations. And it was the most curious little sentence. I don’t even know if it was a complete sentence, just a few topical ideas. That was a good prompt because it made me reflect on what I’ve been observing and how I can communicate it to the audience in a way that shares the lessons I’m learning and validating or reinforcing or even unlearning through my leadership journey.
When I think about why accountability is important, it is because it is the foundation of being able to lead. When you are able to have a strong, introspective, and grounded relationship with yourself, accountability and discipline then become part of your core philosophy, your core beliefs, your core identity. It becomes something very real, this sense of accountability, personal and self-accountability, and it creates a reinforcement loop. It becomes a recursive process where you think about discipline, you think about accountability, and you think about where there may have been deviations or missteps. It creates awareness, this accountability awareness loop.
It also helps when you’re thinking about the weight of leadership. It helps you realize that you should carry this sense of accountability. I mean, at the levels most of your guests operate, people I engage with, they are responsible for hundreds or thousands of people, for hundreds of millions or even billions of dollars. There is a responsibility that is simply required to sit in that chair. You have to have a strong ability to respond, which means having a deep relationship with yourself. You need to know where your convictions are. You need to be able to separate the noise, because you are going to get a lot of noise at that altitude. You are going to get a lot of input. You are consuming a lot of information and data.
So it is important to have ritual, routine, and self-accountability so that you know you are making the best decisions. My job is really about making the best decisions, having a definition of where we want to go, and then making the decisions that allow us to get there, in both the near term and the long term, while ensuring that what I want is good and aligning the organization to that. When you strip it all down, all of that is about accountability, being accountable to the results, to shareholders, to employees, but ultimately to yourself. Because when you can be accountable to yourself, everything else falls into place, and then you are leading from your most authentic space. That is the hot take that has been on my mind since you gave me that prompt. Where do we go from here?
Adam: That’s going to be my question to you. Where do we go from here? What can anyone in a leadership role do to hold themselves more accountable?
Darryl: I can only speak to what has worked for me and what I communicate when others ask me this question or when I am coaching executives from a board position. Create space. Create a lot of space. More space and more margin. I think we are conditioned to ignore silence and see it as weakness. We want to fill the void. We are not truly comfortable with silence.
But the purpose of silence is processing. It is for synthesis. It is to allow the neocortex and prefrontal cortex to actually connect those neurons, those ideas, those thoughts. You need space for that. Without space to reduce noise, it is hard to know if you are on or off discipline, if you are being accountable or not, if you are carrying the responsibility well or not. You have to be the barometer because everyone else around you will have different motivations. They are separated from the vision and the mission. My role as a leader is to hold the most pure essence of that mission. Any communication downstream is diluted simply because it is interpreted through someone else.
So what does this look like in practice? I am not going to say it is meditation. That is too trendy, too simplistic. Most people do not even understand what meditation really is. Sometimes, it is just not opening your smartphone for 10 minutes in the morning and jotting down what is on your mind. It is taking a few extra minutes in the shower to think something through. It is telling your team, I will decide in two days instead of right now. If your reflex is to respond immediately, then delaying your response intentionally is a practice.
So do not call it meditation. Call it incremental margin. And do not fill it with anything, not email, not podcasts. Just space to think. And if you are thinking, I do not have time for that, you have to make time. Five or ten minutes. Just take it all off. Something will come to mind. Do not dismiss it. That is what meditation teaches us, freedom of thought.
If there is something recurring, like a revenue target or a team structure issue, ask yourself why it keeps surfacing. Follow the thread. Even five or ten minutes can make a huge difference.
The second thing that works for me is reducing the flow of information. Creating better boundaries and filters. We often suffer from availability bias. We are too available, too plugged in. Slack, Teams, Zoom. Not all information is good information. If I am receiving everything, that is a signal I have not built strong decentralized command. If I am reacting to everything, I do not have good systems.
That used to feel like founder mentality, being involved in everything. But now I control the flow of information. I set windows for checking email and Slack. I set expectations. If there is an emergency, call me. Pick up the phone. You teach people how to engage with you.
This all goes back to accountability. If you cannot be accountable to yourself, if you cannot say, I am not going to respond to that right now, then that is an internal issue. Until you resolve it, you are not being the most effective leader. You become the limiting factor.
Adam: How can the people around you help you hold yourself accountable? What role would an accountability buddy or a coach play? What kind of tools can you lean on as a leader to hold yourself accountable?
Darryl: You have to build that around you. For senior executives, CEOs, board members, SVPs, VPs, whatever scale you are at, you need an accountability infrastructure. You need people around you who are both incentivized and motivated to see you win. They should be aligned with your values and deeply aligned to your mission.
Most people listening to this podcast likely have some version of an executive assistant, a gatekeeper, or a Chief of Staff. If you do not, that is the first hire to make and make it well. You need to build a trusting relationship with this person. They are going to see you breaking before you see it in yourself. They need permission to say, you may not need to go this week, or you are missing three priorities.
For me, that is Michelle Huey. She is involved in every part of my life, from board work to family to the angel investing office. She understands my capacity and my priorities, from parenting my teenage daughter to leading a company. So number one, get it right with your closest operator, whether that is a Chief of Staff or EA.
This is not something AI can replace. AI cannot observe your scattered notes and realize you might just need a day to read. That nuance is missing.
Number two, align with your partner at home. Or a friend. Share your challenges. Make it real. Sometimes all it takes is someone saying, hey, just do it.
You need honesty. As you climb higher, people start saying yes more often. You need someone who will say, I trust you, but have you thought this through. You need someone who can help you wrestle with difficult decisions, personal, organizational, whatever.
You can white knuckle it for a while, but eventually, you need an external feedback loop. Someone to hold the mirror up and say, that was a good decision, or do you know the impact of that no you gave. That mirror could be your Chief of Staff, your EA, or your spouse.
Write. This changed everything for me about seven years ago. The act of writing things down, long-form, reflective writing. You would be amazed at what happens on a five-by-seven note card.
Write every day. It can be, this awful thing happened, or I was disappointed by that. Read what you write occasionally. Do not make it rigid. Just write what is on your mind. Make it observational. Take little notes.
When you read it back, you will see themes and patterns. You will see different versions of yourself. Writing helps separate rumination from actual processing. Everyone can get a pen and a notebook. It is scalable. It is accessible. It is not the answer you would expect from a tech CEO, but it is my most consistent practice. I write a lot.
Writing slows your thoughts down. You can only write so fast and still read it. So it slows you, and in that process, you are already creating accountability. You are writing your word. That is why we sign things. There is a cognitive effect.
When you write, you find your voice. You can see if it is accountable or passive and indifferent. The tone sounds different. You will know when you are avoiding something. And sometimes, by the time you have written it down, you have already decided to do it. Writing is a repeatable, accessible tool for accountability.
Adam: What are cross-functional teams, and why are they so important?
Darryl: I do not think anything is done by individuals alone. There is no such thing as a self-made person. People say, I am a self-made billionaire, but you did not do it all on your own. You had an enterprise, a team, at least an attorney, a tax advisor, or something like that. You need cross-functional teams if you are going to get multidisciplinary things done.
I think we have a really good relationship with understanding single-threaded things. If this, then that. But we do not have as strong a relationship with multi-threaded systems. We also do not have a strong relationship with true team-based dynamics. Most people have not played team sports, so they do not know what it is like to pass the ball, be in flow, take a step back, and trust someone else. What we are learning from those environments is that it takes multiple perspectives and roles to move forward.
That is how you gain efficiency. Through cohesion and cooperation. The most cooperative societies, organizations, and communities are the most effective. We are not taught cooperation deeply. We are told to share as children, but not why sharing matters or when it does not. It becomes a black and white rule. That has to be unlearned in organizations.
Most organizations operate in silos. They achieve results but in very inefficient, fragmented ways. I have worked in turnarounds, restructuring, distressed asset management, scale transformations, and innovation cycles. These are environments where things are breaking down. Most of the time it is because of lack of cohesion and too many things happening at once.
In the organizations I have assessed, been part of, or helped restructure, the problem often comes down to noise, fragmentation, and isolation. There is no shared belief system. Departments are entrenched, fear-based, and individualistic.
A good test for cross-functionality is during a town hall. Go three levels down in various departments and ask what people understood. See what the follow-up was. When information flows consistently and goals align across departments, then you have true cross-functional collaboration. It is not a relay race. It is a dance, a constant handoff.
When you see dependencies like engineering handing off to marketing, then to sales, then to customer success, you know those overlaps are real. If your goal-setting system, whether OKRs or something else, does not show cross-threaded goals, that is a red flag. Cross-functional collaboration aligns the entire company around outcomes.
For example, at Aspect, we focus on net revenue retention. That is one of our core performance indicators. Everything, including engineering and even my executive assistant, ties back to that outcome. We have created overlap where needed. Sometimes we overdo it and then have to dial it back. It is about refinement.
You can test this with information flow and goal alignment. And here is the benefit. It creates a performance culture. It creates shared outcomes. That helps HR and performance management. We want to retain high performers, coach the middle group, and deal appropriately with the lower quartile.
When an organization is not cross-functional, you hear things like, that is not my fault, that was another department. You smiled because you have heard that before. Finance blaming engineering, for example. That would rarely happen in a truly cross-functional culture.
We need to build for that. Leaders need to imagine what true cross-functionality looks like. Spend two hours on this. What would your cross-functional utopia be? Maybe finance should be in engineering calls. If they are not, ask why. What are they doing that is more important? Maybe the monthly retrospective is where the conversation happens. If finance hears that the product team is changing packaging or monetization, maybe they need to rethink SKUs or tax treatment.
You have to take time to ask, what would the ideal outcome be? Then bring others in. Invite someone like Jack to think with you. Do not let him just complain. Ask what utopia would look like. Often, Jack says something simple like, it would be cool if this person were in that meeting. Create those spaces. Do not do it in isolation. Bring in contributors you do not normally involve. Find those individuals and let them help ideate cross-functional collaboration.
Adam: If you’re working on a cross-functional team, what do you need to do to be successful?
Darryl: It depends on your role, but I will try to generalize. If you are on a cross-functional team, do not hold back. You need conflict, debate, perspective, opinion. You are not attacking people, you are attacking problems. But what I often see is that the person with the most valuable opinion sits quietly and says nothing. That is a problem.
Everyone has to speak up. Everyone must contribute. That should be the expectation. We engage. We challenge. Jack, what do you think? Jill, what do you think? Emily? Rashawn?
Another important thing is that the most senior and influential people must go last. You set the context. You say, here is the challenge. We are launching something or fixing something. We are seeing constraints. Here is what I would like us to solve. Now, I want everyone to speak. Reflect on your experience and propose what would work better.
Give people five minutes to think. Then go around the table. Or assign who goes next. Let Adam decide the order. That is how a leader shows up. You curate, nurture, and create space for cross-functional collaboration to emerge.
Often, we try to control the outcome. Instead, we need to control the process so that collaboration becomes the outcome.
Adam: Are there specific times when a cross-functional team is especially important, and are there specific times when a cross-functional team is not the right team to have in place?
Darryl: If you are doing anything at scale or driving growth, you will always need cross-functional teams. That could be internal departments or external partnerships. Maybe you have multiple business units or shared marketing resources. Every organization is different.
If you are going from one to two units, you need cross-functional. As roles become more specialized, you need even more cross-functionality. When everyone was a generalist, there was lots of overlap. When you become highly specialized, the overlap shrinks. And that is when collaboration becomes even more necessary.
This is most common at scale. Companies at 200 million or 1 billion in revenue. At that stage, you do not just need full-stack developers. You need 30 people working just on UI. That is a specialty. They need context. Otherwise, what they create will not connect with strategy.
The more you scale, the more you need cross-functional collaboration. Especially when working with external firms. Big four consultancies or global agencies. Maybe you are working on a Super Bowl ad. These engagements often have client and agency tension. The client does not know how to brief properly. The agency does not know how to ask the right questions.
This comes from an absence of principles around collaboration. If you are early in your leadership career, start now. Build this muscle early. If you are leading 20 people, it is a great time to start. That way, when you get to scale, it will feel familiar.
In large organizations, it may take two to four years to build. In the biggest ones, maybe never. So start early.
Adam: Do you have any other best practices to follow or pitfalls to avoid when it comes to working on or building or leading cross-functional teams?
Darryl: I will double down on three things. Transparency, communication flow, and space for healthy conflict and debate.
You cannot have cross-functional collaboration if you are not dealing with reality. And you cannot deal with reality if you are missing perspectives. If people in your cross-functional teams are not sharing authentically or efficiently, then you might as well not have the team.
That is a hot take. Is it better to have a cross-functional team that is fake and quiet, or to stumble through building a real one? I would choose honesty every time. If you create honesty, you will naturally create diverse and valuable perspectives. That is where real collaboration begins.
Adam: Darryl, thank you for all the great advice, and thank you for the fun conversation.
Darryl: Thanks for having me. It was a great conversation. If I can connect with anyone or if you want to discuss any of the ideas we talked about, visit linkedin.com/DarrylKelly. I would love to engage in any conversation this might have sparked.
