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Guest: Matt Dunie, a coach at CEO Coaching International. Matt has founded or co-founded four companies and served as CEO or President five times across the information services and SaaS sectors. He’s led businesses ranging from startups to enterprises approaching $400 million in revenue, and he’s executed more than 20 acquisitions and exits.
Quick Background: Successful startups and small businesses eventually reach a place where complexity starts to stall growth. It’s at this early turning point that the CEO has to take their leadership up a notch and make the tough decisions that will Make BIG Happen.
On today’s show, Matt Dunie discusses how to navigate the challenges of the “messy middle,” including dealing with change, decentralizing decision-making, and finding the courage to lead with transparency and empathy.
Keys to Pushing through the Messy Middle From Matt Dunie
1. Professionalize Your Company
“Being professional is different for me than it is for somebody else,” Matt Dunie says. “The point is that you’re looking for a destination to take the grind away from the business, to get away from the messy middle, to work towards something that is much more scalable, much more efficient, much more profitable, that is sustainable over time. You don’t have to be corporate in order to be professional. Being professional is not being bureaucratic. It’s what you want to define it as. And then building towards that.”
When Matt says “corporate,” he’s talking about the systems and specialization that large companies have the luxury of building out. For smaller companies, the path through the messy middle often requires more agility and flexibility. Yes, the CEO has to make some key investments in people and tech to keep the company moving in the right direction. But it’s arguably more important that the CEO learns how to maximize resources by delegating and empowering A players. The less centralized that day-to-day decision making is, the more time the CEO will have to focus on CEO-level responsibilities.
“Professionalization takes a growth mindset,” Matt says. “A growth mindset manifests itself in a better run, more efficient, more scalable business with more people being happier in their daily role. You have 1,440 minutes in a day, and the question is, how are you going to use your minutes that are allocated to the business? And how do you want your team to use their minutes?”
2. Be Intentional About Culture
“Culture is not by accident,” Matt Dunie says. “I think the way you want culture to grow is the leader defines what they want that organization to look like, be like, act like, feel like. What are my business values? How do I want my business to be thought of? And then what actions and activities support those values? What are the proof statements to that value? How do you execute that on a daily basis? Do you treat your customers with full integrity? Are you transparent with them when you have say, a data breach, or do you hide it? Those are big questions. And then the way you act and the way you support those values is the way you grow your culture.”
Building up culture with real thought and intention can also be one of the most cost-effective ways for smaller companies to maintain and even accelerate their growth trajectories. What Matt calls the “psychic income” CEOs can offer via community involvement, education and training opportunities, and collaboration across departments can make employees feel like they’re contributing to something that’s BIGGER than profit. And the connection that the whole company feels to your core values will create a camaraderie that improves teamwork and daily execution.
3. Have the Courage to Prioritize
On the way through the messy middle, CEOs will have to make some difficult decisions. Long-time employees who can’t grow along with the company might need to be replaced. Board members and shareholders might need to hear news they won’t like. New products or services might need a BIG marketing push, or they might need to be scrapped.
We sometimes call these make-or-break decisions “courageous.” But the true test of strong leadership is often the ability to separate what needs to get done from everything else, and using that clarity to guide all subsequent decisions.
“ Courageous leadership to me, is having brutal prioritization of what the business needs to do on a regular daily basis and figuring out what the long-term priorities are that we have to work on over time,” Matt Dunie says. “If I don’t plan it out all the way, just because I like it doesn’t mean it’s the right thing to do it. Being a courageous leader means doing the hard thing. It means having a little bit of rigor that you didn’t have last year. It means putting together a plan more than a budget. It means looking at your team and understanding where your deficits are and what you need to do to upskill your organization. Being a courageous leader is nonstop, 24/7.”
Having that courage won’t make tough decisions any easier, especially when jobs are on the line. But people will respect your decisions if you respect them enough to be transparent about what the business needs and how everyone will be affected.
“ I once had to let a lot of people go because we were doing a merger,” Matt Dunie remembers. “I took on a lot of those layoffs myself, directly. The afternoon of letting 30 people go, one of those people came into my office and said, ‘Matt, I want to let you know you have a really hard job, and you’ve done a really great job at a really hard job. Thank you very much.’ Because we acted with compassion and empathy.”
4. Scale Your Leadership
The messy middle is often the moment when CEOs confront the true scale of the challenge they’re facing as leaders. Instead of managing a handful of people, you’re managing dozens, or more. Instead of scratching out a profit, you’re earning real money that could fuel more growth or vanish with one bad decision. Instead of feeling like you’re running a business, you might feel like the business is now running you.
In business, the best way to beat a challenge is often to grow through it. That’s true of leadership as well. Don’t let your company’s messy middle turn you into a middle manager. Coaching can help both you and your business break through and start Making BIG Happen.
“ Most people in leadership roles, in the messy middle especially, don’t have the experience that others have in larger organizations,” Matt Dunie says. “It doesn’t matter who you are or who you think you are, everybody’s got some level of the imposter syndrome: ‘What am I doing in this seat today? Am I making the right decision?’ Over time, with work and mentorship, and reaching out to others, you learn. And the best thing about being a coach is you get to share those experiences with CEOs earlier in their careers on how to manage other people in a way that is more successful because you’ve had that experience and you can recognize patterns. When somebody is on a sports field, they’re thinking about things, but then they’re acting. The question is, how do you go from thinking to acting without thinking too long? Then acting becomes second nature because you already thought about it years ago. You’re just executing now. That makes it a lot more fun.”
Top Takeaways From Matt Dunie
1. Set a destination and create systems and processes that will get you there.
2. Culture doesn’t just happen, it’s a product of strong leadership motivating a passionate workforce.
3. Respect your stakeholders and they will respect the tough decisions you have to make.
Links:
This CEO Coach Led His Startup Through “Fire” to $200 Million in Revenue – CEO Coaching International’s Jeff Bledsoe explains how his startup achieved a BIG exit.
A Proven Process for Achieving Strong Culture, Rapid Growth, and a BIG Exit – CEO Coaching International’s Anthony Venus discusses the importance of developing a strong company culture, and what his recent travels have taught him about the need for CEOs to lead with passion and purpose.
About CEO Coaching International
CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, the firm has coached more than 1,500+ CEOs and entrepreneurs across 100+ industries and 60 countries. Its coaches—former CEOs, presidents, and executives—have led businesses ranging from startups to over $10 billion, driving double-digit sales and profit growth, many culminating in eight, nine, or ten-figure exits.
Companies that have worked with CEO Coaching International for two years or more have achieved an average revenue CAGR of 25.9%, nearly 3X the U.S. average, and an average EBITDA CAGR of 39.2%, more than 4X the national benchmark.
Discover how coaching can transform your leadership journey at ceocoachinginternational.com.
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