The Seven Sins of Post-Deal Leadership

A few years ago, I made payroll with cash that should have been set aside for PAYE. In doing so I avoided immediate collapse but I soon had HMRC letters, debt collectors, and I even lost the skin pigment on my forehead due to stress. EOS saved my company. It gave me structure when I was running on adrenaline and hope. It turned panic into productive action and eventually let me rebuild and exit.

I don’t teach EOS because it’s increasingly fashionable. I teach it because it worked for so well me when nothing else did. Since then, I’ve coached many leading UK acquisition entrepreneurs - smart, credentialed, ambitious. Most repeat the same mistakes. They buy a company, take the CEO seat, and within months they’re spinning. Not from laziness or incompetence, but because the skills that won them the deal often don’t map cleanly to first time operational leadership. Deal-doers love analysis and building consensus. Operators live in decisions, often uncomfortable ones. That gap is what causes many searcher-turned-CEOs to crash in transition.

Thankfully, a ‘golden rule’ of search is to buy a company that is sufficiently robust to withstand a couple of years of rookie leadership - meaning most emerge in good shape eventually, albeit with battle scars! If you’re a searcher in or preparing for the struggle of being CEO, here are 7 sins to watch out for.

1. Lurching Between Abdication and Micromanagement

Every new CEO promises empowerment - “my style is to back great people and keep out of their way”. Then, shortly after making this pronouncement to their new team, they vanish… until things wobble, when they rush back in and start rewriting emails and running customer meetings. This isn’t hypocrisy. It’s usually fear - of conflict or being found out. The fix is structure. Clear roles, weekly Scorecards and weekly Level 10 meetings where issues get solved, not avoided.

2. Fuzzy Expectations

Vague direction sounds smart. It isn’t. “We need better retention” means nothing until it’s rewritten as a set of activities, owned, and measured. Clarity is achieved through writing and rhythm. If people keep missing commitments, the problem usually isn’t effort - it’s usually your lack of direction or their lack of relevant talent or capacity. You can’t grip fog.

3. The ‘Goldman Sachs Standards’ Illusion

Many search CEOs come from elite environments. They talk excellence, then tolerate average - missed deadlines, sloppy data, late meetings. That gap kills credibility. Culture is what you tolerate. Start small: meetings start on time, numbers are clean, to-do’s done when they’re due. Check the data, close loops, enforce the basics. You are the standard - the one who starts on time and follows through the same week. If you can’t get something done, don’t commit to doing it.

4. Neglecting the Talent Pipeline

Most CEOs postpone recruiting until things “settle.” They never do. Then someone leaves and the whole operation stalls. Hiring is not a support function. It’s your job. Keep a running list of candidates who would raise the average. Talk to one every week. Recruiting before you need it is the only real job security you have. The CEO who doesn’t build bench strength is resigned to managing weakness.

5. Overlooking Future Stars

Every business hides a few people who could lead more than their title allows. They fix problems quietly, ask questions that matter, and often carry loads that aren’t really theirs. Most CEOs miss them because they’re distracted by the loud or the political. Good leaders spot the people who keep fixing things without being asked. Give those people real projects and feedback. Some won’t scale. That’s fine. You’ll still learn faster than if you keep buying experience (or worse, living with mediocre incumbent talent)  instead of developing it.

6. Avoiding Conflict

Harmony feels safe but kills performance. When you dodge hard conversations, standards slide and resentment builds. The retiring owner who sold the business to you at 3–5× EBITDA instead of a strategic at 6–8× probably didn’t have the heart to let Dave in Ops go or the drive to create more enterprise value. But they also didn’t have a whopping great big loan to service and maybe a preference stack or personal guarantee to outrun. You do.

Direct beats dramatic. When someone misses, talk about it early. Ask what blocked them. Agree the fix. Write it down and review it next Monday. EOS gives you the tools - People Analyzer, quarterly conversations, Scorecards. Use them. Good people want clarity. They relax when they see you confronting hard truths.

7. Managing Up Instead of Leading Down

This one steals the souls of newbie CEOs more than any other. They start running the company for the board, not the team. Decks get prettier while execution slows. Perform, but without the theatre. Run the business tightly and let the results speak for you. Send your numbers and plans to the Board ahead of meetings and use your time together to share issues and agree (or in truly hard cases, find) solutions.

The Searcher’s Paradox

Buying the company felt like the summit. Then you realise it was base camp. The skills that closed the deal - analysis, optimism, persuasion - now get in your way. Operating means rhythm, repetition, and decisions made with 80 percent of the data by Wednesday. That’s what EOS gives you: tools and a process you can lean on when emotion kicks in. The smartest founders aren’t often the most cerebral. They’re the ones who decide soonest and correct fastest.

The Emotional Cost of Leadership Debt

This job gets heavy. You’ll be tempted to hide mistakes, pretend to investors, tell your family you’re fine. You might stop sleeping well. Every avoided conversation and delayed decision adds weight. That’s leadership debt. If you’re not careful, it’ll compound until you’re bankrupt (emotionally at least). The only way out is candour. Tell the truth early - to your team, your board, your peers. Good people will help you solve issues when they’re out in the open.

Closing thought - Process, Practice & Peace

Once you’ve built cadence and stopped living in firefighting mode, the job changes. Your perspective elevates from “in” the business to “on” it. For me, I constantly sweep for issues across the various aspects of my life by looping through a framework I call “Process, Practice and Peace”.

A handle on ‘Process’ means that you have a clear and trustworthy mental picture of how to get a given thing done.

There’s no excuse for being weak on Process in the incredibly supportive UK Acquisition Entrepreneurship community. You have great people around you - Paul Quirk with his Buy and Build Accelerator (book onto his latest cohort here), William Abell or Carl Lundberg at Gerald Edelman for financial architecture, and Bryan Shaw at Fox Williams for the legal and governance scaffolding. If you’ve never run EOS, I’ll show you the core Process in a free 90‑minute workshop - no pitch, just a walkthrough of how it actually works (after which you can self-implement if you don't want, or can't afford, a Coach).

Between us (and others like us), there should be very little mystery left about what to do in each situation the average post-deal CEO has to confront.

Where most founders, and indeed I(!), still struggle is in Practice and Peace - doing the work consistently and not burning out while you do it. I set aside time on Mondays and Fridays for 1:1 (no fee - 30mins) experience shares here. If reading this article has surfaced anything new for you, please feel free to book time with me here.

Mary Philip

Squarespace Expert Member, Circle Member & only Squarespace Authorised Trainer in Scotland.

https://maryphilip.com
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