Why Following Your Former Boss Could Be the Worst Career Decision You Make

Most people don't leave companies.

They leave managers.

According to Gallup's 2024 State of the Global Workplace report, managers account for 70% of the variance in team employee engagement, making them one of the single biggest influences on how people experience work. So when a great leader moves to another organisation and asks if you'd like to join them, it's one of the most tempting offers a professional can receive.

Following your boss

But tempting and right are very different things.

I spend most of my week interviewing candidates about why they're looking for a new opportunity. Some conversations are predictable. Limited career progression. Restructures. Better salaries.

Every now and then, a candidate tells me a story that sticks with me.

Recently, I interviewed an experienced HR Director who had left a company she genuinely enjoyed to follow a former manager into another organisation. He had been one of the best leaders she'd ever worked for. He'd mentored her, challenged her professionally, and played a significant role in helping her progress her career.

When he reached out about an opportunity at his new company, accepting felt like the obvious decision.

After all, why wouldn't you want to work for someone you already trusted?

Fast forward eighteen months, and she was sitting across from me looking for another job.

As we discussed what had happened, I asked her one question.

"What due diligence did you do before accepting the role?"

She paused.

Smiled awkwardly.

Then replied.

"Honestly… none. I trusted him."

That answer perfectly summed up one of the biggest career mistakes I see experienced professionals make.

Why Great Managers Make Us Make Emotional Decisions

Before I explain why this can go wrong, it's worth understanding why so many people do it.

Working for a great manager can completely change your experience at work. They advocate for you. Develop you. Give honest feedback. Protect their team. Open doors that might otherwise remain closed.

It's no surprise that when they move elsewhere, talented people are tempted to follow.

There's also a psychological comfort in familiarity. Changing jobs is stressful enough without having to worry about whether your new manager will be supportive. Following someone you've already worked with removes much of that uncertainty.

It feels like the safer option.

But the candidate I interviewed admitted something important during our conversation.

She wasn't really joining the company.

She was joining her boss.

Looking back, she realised she'd spent more time evaluating him than

she had evaluating the organisation.

Those are two completely different decisions.

Why Trusting Your Former Boss Is Not the Same as Due Diligence

There is absolutely nothing wrong with wanting to work with someone you respect.

The problem begins when trust replaces curiosity.

During our conversation, the candidate admitted she never really researched the business because she assumed her former manager already had. She didn't investigate the financial performance. She didn't research the executive leadership team. She didn't ask why several senior roles had recently become vacant. She didn't look into employee turnover.

She simply believed that if someone she respected was joining, it must be a great opportunity.

Looking back, she described it as outsourcing one of the biggest career decisions of her life.

That phrase has stayed with me.

Because it's surprisingly common.

According to research from New Possible, poor leadership and unhealthy culture remain the top reasons employees leave. Yet when candidates follow a trusted manager, they often skip the very research that would tell them whether those problems exist at the new organisation. 

Every candidate should complete their own due diligence before accepting an offer, regardless of who is making it. That means researching the financial health of the company, recent business performance, leadership stability, market reputation, employee turnover, culture, long term strategy, and industry outlook.

Your former boss may have answered those questions for themselves.

But they haven't answered them for you.

Why You Are Joining a Company Not Just a Manager 

Joining a Company Not Just a Manager 

One of the biggest misconceptions candidates make is believing that a great manager automatically creates a great workplace.

Managers matter enormously.

But they don't control everything.

Even exceptional leaders can't single handedly overcome poor executive leadership, a toxic culture, weak financial performance, constant restructures, or a lack of investment.

The HR Director I interviewed loved working for her former manager.

What she didn't appreciate was that he was also walking into an unfamiliar environment.

Within months of joining, budgets were frozen. Projects were cancelled. Senior leaders started leaving. Business priorities changed repeatedly.

None of those decisions sat with her manager.

They were organisational problems.

When people follow great leaders, they often assume they'll recreate the same positive environment they experienced previously.

Businesses don't work that way.

The company you join has far more influence over your daily experience than one individual ever will.

Your Former Boss Is Starting From Scratch Too 

Another point that's often overlooked is that your former manager is also new.

In your previous company they probably had strong relationships, organisational influence, political capital, trust from senior leaders, and years of institutional knowledge. They knew how decisions were made.

Who influenced them. Where to go for support.

All of that disappears when they move.

They're now learning new systems. Building credibility from scratch. Working out who the real decision makers are. Understanding an entirely different culture.

The leader you remember is still capable.

But they're operating in completely different circumstances.

A manager who is new and still finding their feet is even less likely to be in a position to invest in your development in the early months.

It's unrealistic to expect exactly the same experience simply because you're working together again.

The Questions She Wishes She'd Asked

As our interview continued, I asked what questions she'd raised during the recruitment process.

She admitted there weren't many.

Most conversations centred around the role rather than the company. She assumed she already trusted the most important person involved.

Looking back, she said there were several questions she wished she'd asked.

Why has this position become available? What are the biggest challenges facing the business today? What does success look like after twelve months? How has the company performed over the past three years? What is the long term strategy? What are the biggest risks someone joining now should understand?

These aren't difficult questions.

But they're often the ones candidates forget to ask when they already know the hiring manager.

Ironically, they're also the questions that reveal whether you're joining a business with momentum or one facing significant challenges.

One comment she made towards the end of our conversation really stood out.

"I ignored a few red flags because I trusted him."

That's probably the biggest lesson from her experience.

Trust is incredibly valuable.

But it should be the result of due diligence, not the replacement for it.

7 Questions Every Candidate Should Ask Before Following a Former Boss

Following a Former Boss

If you're considering joining a former manager at a new company, don't let familiarity do all the thinking for you. Before accepting any offer, work through these seven questions.

1. Would I Still Take This Job if My Former Boss Wasn't There?

This is the most important question in the entire article.

Strip away the relationship and evaluate the opportunity objectively. Would you still be excited about the role? Would you still be interested in the company? Would you still believe it's the right move for your career?

If the answer is yes, then having a trusted manager there is simply an added bonus.

If the answer is no, you're making a decision based on one individual rather than the opportunity itself.

2. Why Is This Role Actually Available?

Not every vacancy exists because a company is growing.

Sometimes people leave because of poor leadership, unrealistic expectations, burnout, or organisational instability. Ask direct questions. Is this a newly created role? Who previously held the position? Why did they leave? Has the structure changed recently?

Good employers won't be offended. In fact, they'll usually appreciate candidates who want to understand the business before making an important decision.

3. What Is the Financial Health of the Business?

One of the easiest mistakes candidates make is assuming a successful looking company is a successful business.

Spend an hour researching before you accept an offer. Look at recent financial performance, funding announcements, major client wins or losses, expansion plans, recent restructures, and leadership changes.

A little research now can prevent a very expensive mistake later.

4. Have I Met Anyone Besides My Former Boss?

This was another point the candidate admitted she'd overlooked.

Every conversation she had during the process revolved around the person she already knew. She never really got to know the wider leadership team.

Whenever possible, meet future colleagues. Speak with cross functional stakeholders. Understand how decisions are made.

One great manager can make your working life enjoyable. An excellent leadership team can transform your career.

5. What Do Employees Say About Working There?

Every organisation has strengths and weaknesses.

The key is understanding what they are before you join. Speak to people in your network. Read employee reviews with a balanced mindset. Look at LinkedIn to see how long people stay. Is there a pattern of senior leaders leaving after twelve months? Are employees being promoted internally?

None of these things should make the decision for you. But together they build a much clearer picture of the organisation you're about to join.

6. Does This Opportunity Move My Career Forward?

It's easy to focus on who you'll be working for.

Instead, focus on who you'll become. Will you learn something new? Will you develop new skills? Will this improve your long term marketability? Does this role bring you closer to your career goals?

Every career move should create momentum.

Don't move sideways simply because someone you trust asked you to.

7. What's the Biggest Risk of Joining This Company Right Now?

Every organisation has challenges.

Strong leaders are honest about them. Ask: "What do you see as the biggest challenge someone joining this team will face over the next twelve months?"

The answer usually reveals far more than a polished employer branding presentation ever could.

When Following Your Former Boss Does Make Sense

Despite everything I've written, following a former boss isn't automatically a bad career move.

I've seen many candidates build incredibly successful careers by joining leaders they trust. The difference is that they still completed their own due diligence first. They weren't joining because their former manager asked them to. They were joining because the opportunity made sense.

Following a former boss can be an excellent decision when the company has a strong reputation and clear growth strategy, you've met the wider leadership team and feel confident in the organisation, the role offers genuine career progression, the business is financially stable, the culture aligns with your values, and you'd still accept the offer even if someone else were managing you.

That's the difference.

A trusted manager should strengthen an already attractive opportunity.

They shouldn't become the opportunity.

Conclusion

The HR Director I interviewed wasn't inexperienced or careless.She simply placed so much trust in a leader she admired that she stopped asking the questions she would normally ask.

Looking back, she didn't regret working for her former boss.

She regretted not properly evaluating the business before she joined.

The next time a former manager calls with an exciting opportunity, don't automatically say yes and don't automatically say no either. Take the time to understand the company, meet the wider leadership team, and decide whether the opportunity genuinely supports your long term career goals.

If the answer is still yes, then having someone you already trust is simply the icing on the cake.

If you enjoyed this article, you may also find these useful.  How to Manage a Job Offer When You're Waiting on Another explores how to handle competing timelines professionally without damaging the relationships that matter. 12 Interview Culture Questions that helps reveal company culture And How to Evaluate a Job Offer: A Comprehensive Checklist.