The perks and perils of employing your former boss

What’s it like to lead with your former boss in the room, now in a junior position to your own? As David Cameron made his way into Number 10 this week to be named as foreign secretary, business owners have their own views on the leadership dynamics going forward.

Cameron hasn’t sat around the Cabinet table since 2016, when he quit as Prime Minister after the Brexit vote. At the time, current Prime Minister Rishi Sunak had been elected as MP for Richmond after a stint working for Cameron’s Conservative Party.

Some fear Cameron’s ‘older statesman’ presence in government could put the younger Prime Minster off his stroke.

“Boundaries, boundaries and more boundaries!” is Melissa Howard’s advice to Rishi Sunak, after going through a similar experience. “Prioritise maintaining a high level of professionalism and formal communication, as you would with any team member”.

Finding a new footing

Howard, a former NHS administrator, started her career in the health service working for her mum, who was the manager of a large GP practice. Over 15 years later, she took her mother on as an associate in her own business, web and graphic design service MDH.

“Be prepared for the unique emotional dynamics such a role reversal might entail,” she warns.

Melissa’s situation added family dynamics into the mix, but even those without these complications say the transition is tricky.

Kraig Kleeman, founder of sales outsourcing business The New Workforce, ended up being the boss of his own former boss – who became the vice president of sales at his company. While he says the relationship worked because of the “secret sauce” of their close friendship and teamwork, he acknowledges it was hard to get started.

“Both sides expected a seamless transition because we worked well together in the past, but our reality did not quite fit this altruistic approach,” he explains.

“My ex-boss did not find it easy to go from being the top dog to reporting to me. Different leadership styles and ideas about who’s in charge did lead to conflicts.”

Josh Amishav, founder of cybersecurity group Breachsense, has been through something similar. “It was initially difficult to separate our past relationship from our current one,” Amishav tells us of hiring a former manager.

Fostering new dynamics

Open lines of communications are key to making these new relationships work, say employees-turned bosses.

Kleeman says that a frank discussion at the start of the new working arrangement saved a lot of pain later.

“Define roles, responsibilities, and how to navigate this new situation,” he advises. Once you’ve had this chat, the boundaries set will need to be kept in mind continually.

“Avoid personal drama and act professionally to create a positive work atmosphere.”

Giving a former boss a level of personal responsibility can help remove feelings of frustration, Amishav counsels.

“Having clearly defined roles and responsibilities helped avoid confusion around responsibilities and decision-making. A few things that helped make the relationship successful were communicating expectations and tasks very clearly and then giving him autonomy to execute,” Amishav says

Howard adds that revisiting the health of the relationship frequently can also save pain.

“Regular check-ins and feedback sessions are crucial to ensure both parties adapt well to the new dynamic. Always keep your focus on the business goals, ensuring that decisions are made in the best interest of the company. And importantly, don’t forget to celebrate your joint successes, as they are vital in fostering a successful and harmonious working relationship.”

A worthwhile struggle

While new power dynamics can be tricky to establish, Rishi can take heart from business owners who say the role reversal can bring benefits too.

Kleeman points out that one of the perks of employing a former boss was knowing what he was getting.

“When I had worked with my ex-boss before, I had the inside scoop on their skills and quirks. That was super helpful in making the most of their talents,” Kleeman says.

“We already had trust, which created a positive workplace where everyone felt valued and motivated.”

Amishav agrees that he valued the skills and experience brought by ex-boss, now an employee. “The primary advantages were leveraging my former boss’s experience and connections. There was certainly some knowledge transfer and mentoring happening.” Howard adds that, when the going gets tough, keeping your eye on the benefit of the changing relationship will help get you through.

“You get to establish a trusted working relationship with someone who truly understands you, including your strengths, weaknesses, and can swiftly pinpoint your blind spots,” Amishav tells us.

“However, it’s equally important to stay aware of potential risks. These include changes in relationship dynamics, the possibility of breakdowns, boundary issues, and the risks associated with favouritism.”

It’s certainly something to keep an eye on, post cabinet reshuffle.

Rosie Murray-West

Rosie Murray-West is a freelance journalist covering all aspects of personal finance, as well as business, property and economics. A former correspondent, columnist and deputy editor at The Telegraph, she now writes regularly for publications including the Times, Sunday Times, Observer, Metro, Mail on Sunday, and Moneywise magazine.