Alan Whitman (@AlanDWhitman) header
Alan Whitman (@AlanDWhitman) profile picture

CEO at Nichols Cauley | Building a Modern Financial Services Company in Public | ↓ BREAK THE MOLD™ - Weekly newsletter for pro services leaders

Marco Island, FL
Joined March 2015
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"Go build a business, not a practice." I've said that to a lot of partners over the years. Here's the difference: Growth asks: How do I grow my book of business? Scale asks: How do we build a business that grows without me? Growth on its own can be temporary. Scale produces growth that's predictable and sustainable. It requires defined systems, layered revenue models, horizontal collaboration, and shared accountability. So stop looking at a company as a culmination of partners' books of business. Start looking at each practice as a business within the greater business of the firm. A $100m company could easily be five $20m businesses. Scale each business, and you'll scale the company. Why does scale matter? Because scale: - Produces more financial and intellectual capital - Leads to more sustainable growth - Helps you withstand downturns - Increases your valuation Scaling a business isn't about squeezing more out of individuals. It's about building the business to grow itself. #growth #scale
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I’m not focused on “keeping up” with the latest AI and tech advances simply for the sake of trying to adopt and stay on the cutting edge. That’s not the game we’re playing at Nichols Cauley, and there’s no sense in us trying to be the next OpenAI, Anthropic, or Google. That’s not our strategy. Frankly, I don't think any of us are “keeping up” because there is no one singular benchmark. So, in a business landscape of rapid change (the pace of change is more rapid today than at any other point in my career), here’s what I measure against: Are we evolving at a fast enough rate that the gap between us and those around us isn't widening? Are we continuously evolving into a better version of ourselves? While we don’t have to be first or on the cutting edge, we have to make sure we're not on the verge of irrelevance. We need to ensure we have sustainable, repeatable, maybe a little oversized progress. Gradually, gradually, gradually…we continue to adapt, improve, and embrace new ways of thinking and working (including more use of AI and other technology). And suddenly, we are a lot different from what we were just a couple of years ago. That’s the game most of us are playing. Continuous evolution. So I’d encourage leaders not to focus so much on “keeping up” with the pace of change and technology adoption simply for the sake of trying to keep up. It’s a bar that’s both unclear and always moving. Focus on the game you’re playing. Focus on your strategy. Focus on continual improvement. I bet you’ll like the results. #ai #strategy
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A stance I’ve adopted in my leadership career: Don't tell me we can't do something. Because we can do it. There’s just a cost and roadblocks to overcome. While some things might not be plausible at a given moment in time, nothing is impossible. So I simply won’t accept the answer of “we can’t do it.” Instead, I challenge my leaders to tell me what it's going to take. Go through the exercise of defining the roadblocks that need to be overcome and the steps that need to be taken. Then we'll decide whether we want to do it or not. Is it going to take money? Define how much. Is it going to take time? Define how long. Is it going to take more headcount? Define who. Is it going to take new skillsets? Define what they are. I’ve had people shy away from pursuing certain opportunities because they were going to be hard… Well, of course it's going to be hard!! Business is hard. Hard doesn’t equal impossible. And, from my experience, accomplishing something very hard is an incredibly rewarding experience. So I don’t accept “we can’t do it” as an answer. I challenge my leaders to define “What will it take?” And whether we decide to pursue it or not, at least we’ve defined the path. No matter what, that’s a valuable exercise.
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My mother used to tell me: “Don't wish your life away.” I’d say I can't wait for this. I can't wait for that. It's like in boating. Is it the destination, or is it the journey? A lot of boaters want to get there as fast as they can. Well…what about the journey to the destination? I admit I tend to be an instant gratification guy… I want it now. I want to see our efforts and work show up in the P&L. And sometimes the results don’t show immediately. So this is my reminder to myself and every other leader out there: We’ve got to have patience. We’ve got to set a strategy, commit to the intentional disciplines, and we’ve got to pay attention to the signs. We’ve got to celebrate the small wins. Because one thing I’ve seen play out again and again: small wins add up to become big wins. Enjoy it, my Mother would say. As frustrating as it may be to acknowledge, she was right, of course… So remember to celebrate the small wins. You can’t get to the big ones without them. Have a great weekend, everybody.
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I've been told I’m too aggressive in goal setting. Like telling our leadership team at a $700m company we were going to grow to $1.5B in 5 years. Here’s why I believe in doing it: 1. It’s ok to state the WHAT even when the HOW isn’t clear. I didn't have a step-by-step plan to double our revenue. But we did have a strategy that was our guidepost. So I believed that if we told people the WHAT and they believed in our vision and mission, we would collectively figure out a way to get there. Spoiler alert: It worked. And we got there 2 years ahead of schedule. 2. Underestimating ourselves is part of human nature. We tend to set more achievable goals because we're not sure if we're capable of achieving more. So we default to something safer and more comfortable. I believe we’re much more capable than we think we are. And a great leader’s job is to challenge and enable people to accomplish more than they thought was possible. So, yes, I believe in setting stretch goals. AND I believe the way they are communicated is critical. You have to know your audience and be able to paint a picture that inspires people, not just scares them. Then the real work begins…the leadership of continuously enabling people to accomplish more. It takes things like changing mindsets, getting buy-in, intentionally developing people, communicating, and constantly seeking to gain alignment. That’s how you enable people to accomplish big, lofty goals. And that’s why I believe in setting them in the first place. #leadership
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We’re still hiring more people at Nichols Cauley because we need people to drive and implement progress within the organization. Including technology & AI efforts. We're a professional services organization. And while we’re finding ways to implement technology to take care of more of the “doing”—the work— there’s still the strategy, development, launch, and consistent monitoring and refinement of these processes. I maintain that humans are critical to deliver that work—the strategic thinking and the judgment. And I don’t see that changing anytime soon. Plus, frankly, I'm just not going to sit around a table with a bunch of bots… Businesses are built and maintained on relationships, and AI advancements haven’t changed that. So we’re bought into technology & AI advancement at our company. We’ve rolled out a number of initiatives, and @Greg Stone is working on more. We’ll continue to find ways to use it to reduce unnecessary human touches and allow our team to focus on the highest value work. Work that I’ve yet to see a machine do more effectively than our people. We’re building something special at Nichols Cauley, and we’ll continue to do it with great people enabled by technology. I invite you to come join us: bit.ly/4vmPKU9
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Leaders: We can’t forget that before we get the lagging indicator (numbers in the P&L), we’ve got to define and execute the leading indicators: The activities. The engines. The early metrics. The INTENTIONALITY needed. Numbers on the P&L are a result. A result of what? All the great enablers and actions that go into making those numbers possible. Do the necessary things and the results will result.
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It’s an unpopular opinion because it’s not newsworthy… but everybody's got to stop trying to find a problem that AI can solve. That mindset needs to be inverted. The goal should be to continue to improve your business, with AI & technology being a potential solution. I know that mindset won’t gain any headlines, AND I continue to think it's the right play. The question isn’t: “How do we use more AI?” The question is: “How can we minimize unnecessary human touches and reduce friction?” The goal is to create greater efficiencies and more capacity by reducing friction. How we do it (i.e. the specific tools used) matters less. So while companies are pushing AI usage to try to solve every single problem, we’re doing something different. We’re trying to eliminate friction and enhance capacity. That’s a completely different mindset. #ai #technology #growth
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It’s funny…I’ve talked to leaders leading $20B professional services companies and others leading $20m companies. The things they’re solving for are almost identical. We’re in people businesses, and when people are involved, the leadership challenges, roadblocks, and opportunities have an uncanny similarity. We’re all trying to: - Overcome human nature - Shift mindsets - Gain buy-in and alignment - Challenge people to adopt new ways of working - Push people out of their comfort zone - Have the hard conversation instead of the easier one - None of that gets simpler or goes away with a bigger balance sheet. I’ll never forget when one of my leaders said, "Alan, it's not about what you're asking people to do. It's about what you're asking them to leave behind." That’s the foundational work every leader in professional services is up against—overcoming human nature. It may take different forms, but every leader is much more alike than different in the things we’re trying to overcome to to remain relevant and sustainable. #growth #professionalservices #leadership
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I’m excited to share that I’ll be speaking at the Bridging the Gap Conference this year! WHERE: Charlotte, North Carolina
 WHEN: July 28-30, 2026
 THEME: The future of accounting is built differently: where wellness meets results. I’m excited to be part of a group that’s progressing the profession forward and doing it in a sustainable way. Hope to see many of you there! 👉 Check out the agenda and see what’s planned: btgconference.com/agenda/ @TriMerit
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Someone recently asked me if I worry about competition. The honest answer is no. But don’t hear what I’m NOT saying. I’m not saying I don’t consider them, I just don’t allow myself to get caught worrying about them. And not because I think we're better. I don't lead with that. I respect what plenty of other companies are doing. There are sharp operators out there and lots of people I admire in our profession. That said, if I concern myself with what others are doing, I can easily get consumed by it. I’ll be chasing ghosts. I'll be reacting to their playbook instead of executing our own. Instead, I see the road to building a relevant and sustainable organization as a windshield-focused pursuit. Eyes ahead. Focused on our strategy and what we’ve set out to achieve. We have too much good stuff in front of us for me to be looking sideways or behind. So I'm aware of what others are doing. I read the same articles you do. I take notes from other leaders the same way I take notes from the books I read. Pull concepts and ideas and apply them where they fit. But aware and worried are different things. If you're a leader spending your time tracking and obsessing about the competition, I would caution you. Be aware AND run your own race. Focus on your strategy. Execute as best as you can. Do that, and when you pull your head up to glance around, you’ll like where you are. #leadership #competition #success
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My oversimplified approach to leadership and building a relevant and sustainable organization: Run the right play. Hire talented people. Let them do their job. It’s not easy. And it doesn’t have to be overly complicated.
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One thing is becoming more clear to me: the future of professional services looks a lot like the past. Yep, the apprentice model. A senior partner recently asked me what his role looks like in the new company we're building. I gave him a simple answer: "Keep doing what you're doing. And bring a young professional to every meeting." For decades, we ran professional services on production. You're a young associate, you grind out the work, the firm bills your hours, you build your time, you get promoted, etc... The production was primary because the firm needed to recognize the revenue. Now the production is going to automation. Which means we have a choice. We can act like the old model is the only model, which results in laying off or cutting out the young people. Or we can do what we should have been doing all along — use the production to teach. I remember following John DeStefano (my mentor and retired Cooper & Lybrand partner) around to meetings as a young professional. I sat there. I listened. I learned more from John in those meetings than from any course I took or repetitive task I completed. We stopped doing that traditional apprentice model for a number of reasons, but primarily because we needed production to recognize revenue. Now automation can account for the production. Which means the increased margin can pay for the apprenticeship. So the job of the young person entering the profession is to learn. Some by producing and some by observing. So more senior people, like this partner I’m referencing, keep doing what they're doing. And the up-and-coming young person goes with them to every meeting. Observe. Listen. Learn. That's the future of professional services. The good ol’ apprentice model. Just like how it used to be… #professionalservices #financialservices #people
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“What skills should I focus on?” A college student asked me at our STEP program. My answer was three things. None of them are technical. 1. Communication. Verbal and written. 2. Curiosity. 3. The ability to connect the dots. We can teach you the technical stuff. We can teach you tax. We can teach you audit. We can teach you how to read a P&L. What we can't teach you is to be curious. We can't teach you to give a damn about why something is the way it is. Communication, technically, we can teach. Although it doesn’t seem to happen in the same way it used to. I’ll never forget when my mentor, John DeStefano, sat with me on a Saturday afternoon and went line by line through a technical memo I'd written. He'd read a sentence back to me and say, "what did you mean by that?" I'd answer. He'd say, "Well, that’s not what you wrote." It was the most painful experience of my career to that point. I hated every second of it. Looking back, though, I love that afternoon. He taught me how to communicate. And lastly, in an AI-driven world where information is at our fingertips, the ability to connect the dots, to find associations and parallels, is critical. The technical stuff is table stakes. The other things make a career. #development #leadership #accounting
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Someone recently asked me how I grade myself as a CEO. Great question. The scorecard is two-sided. First is external: — Can I convey a cohesive strategy and vision? Not write it down. Convey it. To clients, prospects, acquisition targets. Anyone who could matter to where this company is headed. — Are people picking up what I'm putting down? M&A targets, prospective clients, industry peers, etc. Does our strategy and how we present it make sense? If not, something about how the strategy is defined or articulated is off. — Am I winning M&A deals on strategy and vision, not by bidding the price up? The second part of the scorecard is internal: — Am I getting people excited to become the best version of themselves? Not the version they thought they'd be when they joined. A bigger one. — Am I showing them a real career pathway? Is career advancement something they can see and touch and that excites them? — Am I making people feel like things are being done with them, not to them? Even when there's a lot of change. Even when the change isn't easy. — Am I shifting mindsets? A CEO who can change mindset can change a business. The rest is execution. Curious to hear from those of you willing to share. How do you measure yourself as a leader? Anything I’ve missed here? #leadership #ceo
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Someone recently asked me how I grade myself as a CEO. Great question. The scorecard is two-sided. First is external: — Can I convey a cohesive strategy and vision? Not write it down. Convey it. To clients, prospects, acquisition targets. Anyone who could matter to where this company is headed. — Are people picking up what I'm putting down? M&A targets, prospective clients, industry peers, etc. Does our strategy and how we present it make sense? If not, something about how the strategy is defined or articulated is off. — Am I winning M&A deals on strategy and vision, not by bidding the price up? The second part of the scorecard is internal: — Am I getting people excited to become the best version of themselves? Not the version they thought they'd be when they joined. A bigger one. — Am I showing them a real career pathway? Is career advancement something they can see and touch and that excites them? — Am I making people feel like things are being done with them, not to them? Even when there's a lot of change. Even when the change isn't easy. — Am I shifting mindsets? A CEO who can change mindset can change a business. The rest is execution. Curious to hear from those of you willing to share. How do you measure yourself as a leader? Anything I’ve missed here? #leadership #ceo
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Someone recently asked me how I grade myself as a CEO. Great question. The scorecard is two-sided. First is external: — Can I convey a cohesive strategy and vision? Not write it down. Convey it. To clients, prospects, acquisition targets. Anyone who could matter to where this company is headed. — Are people picking up what I'm putting down? M&A targets, prospective clients, industry peers, etc. Does our strategy and how we present it make sense? If not, something about how the strategy is defined or articulated is off. — Am I winning M&A deals on strategy and vision, not by bidding the price up? The second part of the scorecard is internal: — Am I getting people excited to become the best version of themselves? Not the version they thought they'd be when they joined. A bigger one. — Am I showing them a real career pathway? Is career advancement something they can see and touch and that excites them? — Am I making people feel like things are being done with them, not to them? Even when there's a lot of change. Even when the change isn't easy. — Am I shifting mindsets? A CEO who can change mindset can change a business. The rest is execution. Curious to hear from those of you willing to share. How do you measure yourself as a leader? Anything I’ve missed here? #leadership #ceo
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Someone recently asked me how I grade myself as a CEO. Great question. The scorecard is two-sided. First is external: — Can I convey a cohesive strategy and vision? Not write it down. Convey it. To clients, prospects, acquisition targets. Anyone who could matter to where this company is headed. — Are people picking up what I'm putting down? M&A targets, prospective clients, industry peers, etc. Does our strategy and how we present it make sense? If not, something about how the strategy is defined or articulated is off. — Am I winning M&A deals on strategy and vision, not by bidding the price up? The second part of the scorecard is internal: — Am I getting people excited to become the best version of themselves? Not the version they thought they'd be when they joined. A bigger one. — Am I showing them a real career pathway? Is career advancement something they can see and touch and that excites them? — Am I making people feel like things are being done with them, not to them? Even when there's a lot of change. Even when the change isn't easy. — Am I shifting mindsets? A CEO who can change mindset can change a business. The rest is execution. Curious to hear from those of you willing to share. How do you measure yourself as a leader? Anything I’ve missed here? #leadership #ceo
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Someone recently asked me how I grade myself as a CEO. Great question. The scorecard is two-sided. First is external: — Can I convey a cohesive strategy and vision? Not write it down. Convey it. To clients, prospects, acquisition targets. Anyone who could matter to where this company is headed. — Are people picking up what I'm putting down? M&A targets, prospective clients, industry peers, etc. Does our strategy and how we present it make sense? If not, something about how the strategy is defined or articulated is off. — Am I winning M&A deals on strategy and vision, not by bidding the price up? The second part of the scorecard is internal: — Am I getting people excited to become the best version of themselves? Not the version they thought they'd be when they joined. A bigger one. — Am I showing them a real career pathway? Is career advancement something they can see and touch and that excites them? — Am I making people feel like things are being done with them, not to them? Even when there's a lot of change. Even when the change isn't easy. — Am I shifting mindsets? A CEO who can change mindset can change a business. The rest is execution. Curious to hear from those of you willing to share. How do you measure yourself as a leader? Anything I’ve missed here? #leadership #ceo
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Someone recently asked me how I grade myself as a CEO. Great question. The scorecard is two-sided. First is external: — Can I convey a cohesive strategy and vision? Not write it down. Convey it. To clients, prospects, acquisition targets. Anyone who could matter to where this company is headed. — Are people picking up what I'm putting down? M&A targets, prospective clients, industry peers, etc. Does our strategy and how we present it make sense? If not, something about how the strategy is defined or articulated is off. — Am I winning M&A deals on strategy and vision, not by bidding the price up? The second part of the scorecard is internal: — Am I getting people excited to become the best version of themselves? Not the version they thought they'd be when they joined. A bigger one. — Am I showing them a real career pathway? Is career advancement something they can see and touch and that excites them? — Am I making people feel like things are being done with them, not to them? Even when there's a lot of change. Even when the change isn't easy. — Am I shifting mindsets? A CEO who can change mindset can change a business. The rest is execution. Curious to hear from those of you willing to share. How do you measure yourself as a leader? Anything I’ve missed here? #leadership #ceo
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