Why Your Team is Killing Your Exit (And How to Fix It with the Right Hires)
A powerful offer. A growing client base. A strong revenue stream.
None of it matters if your team is the reason your business can't scale—or sell.
In this episode of Freedom to Exit, Lani Dickinson unpacks why the wrong hires might be the biggest threat to your exit strategy… and how the right ones can completely change your outcome.
You'll hear how one business owner nearly lost a $30 million deal because of one wrong person—and how strategic, specialized hiring turned the entire business around.
What You’ll Learn:
- Why generalist hires can create chaos and kill efficiency
- How specialized team members boost business value and buyer interest
- Signs your current team may be capping your growth
- The connection between operational stability and exit multiples
- Real examples of companies that transformed by hiring the right people
If you want to step back from the daily grind, grow sustainably, and attract buyers who pay top dollar, it starts with who’s on your team.
Get the Free Changes Assessment: https://stealthfreedomtoexit.com/changes
Want to know where your sales process is broken and how to fix it? Take the Changes Assessment to identify where you're losing leads, how AI and automation can save you time, and how to get out of the daily sales grind
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Transcript
>> Lani Dickinson: Hey, Exit Focus Founders. Welcome back to the Freedom to Exit
Speaker:podcast where we talk about how to build a business that runs without
Speaker:you, scales predictably, and could
Speaker:potentially sell for top dollar when you're ready.
Speaker:Today's episode is about mistake. I see
Speaker:constantly in small business hiring
Speaker:generalist instead of specialist. If you've
Speaker:ever said, I can't afford a cfo so I'll just have my
Speaker:bookkeeper handle the financials. If you've ever hired a
Speaker:family member, a va, or your most loyal employee for a
Speaker:roleya they aren't actually qualified for, or if you
Speaker:feel like you're drowning in operational chaos but can't
Speaker:afford a real manager, you don't have a hiring problem.
Speaker:You have a growth, stopping priority problem. The
Speaker:goal? To get the right people in the right seat
Speaker:so your business can scale and you don't have to be
Speaker:in it. Hiring specialist leads to
Speaker:profitability even though they may cost more.
Speaker:Hiring generalists to save money cost you more in the
Speaker:long run. Buyers actually pay more for
Speaker:businesses with professional leadership. And today I'll show you
Speaker:exactly how my client Mike, with a $10 million H
Speaker:vac company and a $30 million
Speaker:PE turnaround that I did, were able
Speaker:to do that with specialist. The truth is, small
Speaker:business owners think they're saving money by hiring
Speaker:generalists, but it actually costs more in wasted time,
Speaker:inefficiency, lost opportunities, more
Speaker:training needs, more errors, lower
Speaker:productivity, customer dissatisfaction, higher
Speaker:training needs, higher turnover rates. That all is
Speaker:hidden expense that far outpaces the initial
Speaker:perceived savings. Here's what's happening.
Speaker:People have hired a bookkeeper instead of a cpa. They hire
Speaker:a VA instead of a fill in the blank, a podcast editor,
Speaker:a Facebook manager, a social media manager, and then they
Speaker:expect MBA level decision making and strategy.
Speaker:This is rampant in the entrepreneurial space. They
Speaker:hire a jack of all trades office manager instead of a
Speaker:trained general manager who can actually lead the
Speaker:team. They promote their most loyal employee or a family
Speaker:member, even if they're unqualified for a leadership role. So
Speaker:then other people turn over all the time. The
Speaker:result? Bad financial decisions, chaotic
Speaker:operations, inefficiencies, slower business
Speaker:growth, and lower exit evaluations. My
Speaker:client Mike had an HAC business that was being run by
Speaker:all the wrong people. $10 million in revenue, no
Speaker:CPA, no financial analysis, no general
Speaker:manager, didn't even have a lead tech in the H VAC
Speaker:site. His finances were run by, a bookkeeper, and he didn't have
Speaker:any strategic insight. Operations were being managed
Speaker:by someone who hadn't finished High school and had no
Speaker:leadership training whatsoever. She was also
Speaker:irritating the internal staff. He told me he
Speaker:couldn't afford a general manager. His best
Speaker:salesperson was family and signed up for temporary
Speaker:help 10 years ago. So all the sales were
Speaker:dependent on someone who didn't want to be there anymore.
Speaker:And she was missing out on raising her kids. That's a regret
Speaker:they won't be able to overcome later on.
Speaker:What we found. $10,000 a month in
Speaker:unnecessary office supplies, thousands in
Speaker:unused software and subscriptions, and enough cost
Speaker:savings to hire a general manager and the financial
Speaker:expert. We started using, a lead management system with
Speaker:lead scoring and automation that allowed new sales
Speaker:and new salespeople to be able to make a living
Speaker:faster so that they would stay in the company as well
Speaker:as get the family member out of being responsible for
Speaker:sales. After fixing all of this, he
Speaker:got financial visibility and strategic cash
Speaker:management. He hired a real GM and the
Speaker:team was suddenly happier. He's now able to open
Speaker:another location in an unserved market
Speaker:because he has a sales team to cover it. If you think
Speaker:you can't afford the right hire, you probably have wasted cash
Speaker:flow hiding in your business. I did a
Speaker:$30 million turnaround for a private equity company. The
Speaker:biggest problem they had, they didn't hire
Speaker:specialists. They had a bunch of generalists and
Speaker:it was near bankrupt. This company was on the verge of
Speaker:either being divested bankrupt, just
Speaker:shutter the doors. They were backed by a PE firm that
Speaker:had purchased them a couple years before. PE firm was
Speaker:covering $2 million of the payroll and they
Speaker:were done because they're supposed to make at least 20% margins.
Speaker:Right? So the CEO that had been
Speaker:placed there by a family friend prior to the acquisition
Speaker:and stayed with the acquisition had no real
Speaker:management experience and definitely was not ready to function
Speaker:in a PE type environment. Their finances were run by a
Speaker:basic bookkeeper. There was no cash flow forecasting and
Speaker:no financial guidance. They were
Speaker:operating unprofitable service lines that they
Speaker:weren't tracking and they were losing money there, but they didn't even know
Speaker:it and they were taking on risk to lose that money.
Speaker:So what we did, they hired me as a turnaround
Speaker:CEO. I brought in a cfo. Instead of
Speaker:relying solely on a bookkeeper, I hired a
Speaker:collection firm to work old and small balances that had
Speaker:previously been written off and to change our collection
Speaker:process and put in systems. I hired a productivity
Speaker:analyst to evaluate every job in the business. Obviously did a
Speaker:big layoff and we eliminated wasteful roles, streamline the
Speaker:operations, shut down all the unprofitable service lines
Speaker:using data and then we shifted all of those
Speaker:resources into higher margin, scalable
Speaker:operations. This went from being nearly
Speaker:bankrupt and unslable to a $30 million turnaround
Speaker:story that was now sellable and did sell.
Speaker:And we gained the PE teams respect because we
Speaker:built what was needed, built it fast, we didn't waste anymore,
Speaker:and made the hard decisions with data
Speaker:to make things work. Throughout this whole thing, we had to
Speaker:replace the unqualified people with
Speaker:qualified leadership. This is
Speaker:exactly why buyers will pay for a
Speaker:business that has leadership that should be in the business.
Speaker:The specialist, not the generalist.
Speaker:Generalists actually hold a business back while
Speaker:specialists can accelerate the growth. Buyers don't
Speaker:want to come in and run your business. They want your well qualified
Speaker:team to do that and stay and just make the
Speaker:money. Hiring the right financial experts
Speaker:gives you confidence in your decision and improves your
Speaker:profitability. Buyers will pay
Speaker:more for a professional leadership team if
Speaker:your businesses run like a Fortune 500 company, even if
Speaker:you're a small business, you will get paid
Speaker:like It's a Fortune 500 company. So what do you
Speaker:do now? Use our hiring tool to figure out where you
Speaker:could place specialists in your business
Speaker:to get clear ROI on those hires and
Speaker:to build a team that increases your valuation at
Speaker:exit. Get the HR hiring tool in the show
Speaker:notes below. Subscribe and leave a review if you found
Speaker:this helpful. Next week we're going to talk about why branding and
Speaker:competitive advantage matter more than you think. Let's get
Speaker:you free from your business.
