1. THE BUSINESS HAS OUTGROWN YOU
'Some entrepreneurs are great at starting up. Some are great at scaling up. Some can do both. But very, very few can go on to lead and operate a truly scale enterprise,' says Nancy Cruickshank, who sold her fashion and beauty portal Handbag.com to Hearst for £22m in 2006 before launching MyShowcase.com. Be honest about where your skills lie and step back if you're choking a business's growth. Kellie Rixon, former director of people at Macdonald Hotels & Resorts, likens it to parenting a child who's about to go off to university. 'You'll always love it. You've done a great job helping it develop. But sometimes you need to let go for it to mature.'
2. YOU'VE LOST YOUR SPARK
Gareth Jones remembers the moment he knew it was time to 'fire' himself: 'I'd been working really hard in an organisation stifled by bureaucracy,' says the visiting professor at IE Business School, Madrid, and co-author of Why Should Anyone Work Here?. 'I met an old friend for a drink and she said, "What's happened to your twinkle?" I thought, "I'm not losing my twinkle for anyone" - and left the company. When you feel that work is sapping your vital spirit, it's time to move on.'
3. THE BUSINESS IS NO LONGER YOUR BABY
The 'crunch time' for many CEOs comes when their company grows big enough to get outside investors. If there's a new majority shareholder in town and you haven't yet stepped aside to let in a fresh team, the clock's ticking. You're about to become powerless so set yourself a strict departure date and fire yourself before you're brushed aside. 'In any transactional scenario, it's vital to reassess your role,' says Cruickshank.
4. YOU'RE BLOCKING IDEAS
For the third time this month, you feel a warm sense of self-satisfaction: some young people in your business have come to you with ideas for the future - and you've been able to show them that their ideas were both unoriginal and impractical. Does this sound like you? 'The moment you get as much personal gratification from stopping things from happening as from encouraging things to happen is the time to go,' says Jeremy Bullmore, a former creative director and chairman of J Walter Thompson London and MT's agony uncle.
5. YOU'RE A TERRIBLE BOSS
'If you've tried everything and nothing works, or you can't be bothered to try, you're probably just not management material,' says MT columnist Tomas Chamorro-Premuzic, professor of business psychology at University College London and Columbia University, and author of The Talent Delusion (read an extract here). Being a boss is no different than being a musician or an actor; not everyone is cut out for it, and there's no point in forcing ourselves into a role that's not for us. 'Sadly, it's virtually impossible to get promoted unless we become managers, yet most top individual contributors don't perform well when they step up.'
6. CUSTOMERS ARE VANISHING AND PROFITS ARE PLUMMETING
Philip Clarke announced he was standing down as boss of the UK's biggest supermarket within weeks of reporting Tesco's biggest decline in sales in more than 20 years. One of Alan Rusbridger's last acts as The Guardian's editor and leader in 2015 was to leave it with a yearly loss of £45m. Nick Wilkinson chucked in the towel as boss of Evans Cycles last year after reporting a 69% slump in full-year profits. 'In the end we're all judged by our results,' comments James Reed, chairman of recruitment business REED. 'If your team is dropping down the league table, it might be time for a new coach.'
7. MOST OF YOUR COLLEAGUES ARE THE SAME AGE AS YOUR GRANDCHILDREN
John Timpson, chairman of the eponymous shoe repair and key cutting chain, realised he'd reached his CEO sell-by date when he visited one of his shops in Bracknell on his 58th birthday. 'There were three young colleagues running the shop. I added up all their ages and the total was less than 58,' he says. 'It dawned on me that my son James was quicker, smarter and more ambitious than me, so I "fired" myself as chief executive, handed the reins to him and found myself another job as his chairman and mentor.'
8. YOU HATE YOUR SUBORDINATES AND CANNOT REPLACE THEM
Most people are eventually confronted with the unpleasant situation of having to work for an unbearable boss. The reverse is also true. 'Most managers are, at some point, asked to lead uninspiring teams where the talent level is far from impressive and they're not able to replace people,' says Chamorro-Premuzic. 'If you can't fire poor performers or lo-pos (low-potential individuals), you can at least fire yourself as a boss - become self-employed and work for yourself. Most people don't complain about their boss when they are their own boss.'
9. YOUR KIDS NEVER SEE YOU
Even the best job as a big cheese isn't worth keeping if you're having to sacrifice your family life for it. Jones used to be a senior vice president for HR at Polygram International, then the world's largest recorded music company. He loved the job and travelled endlessly - but then came a wake-up call from his kids. 'I had two small daughters and the youngest saw an aeroplane fly over our suburban house and said, "there's Daddy". I just couldn't be that kind of father so I stepped down. It was a tough decision but it was the right one.'
10. YOU NEED A BREAK
Over 13 years, Alexandra Michel at The Warton School, observed a cohort of investment bankers who pushed their bodies to the edge of breakdown. Eating disorders, tics, sleep disturbances, anxiety and depression were commonplace. 'Everyone needs to hit "pause" every now and then,' says consultant Tim Johns, former vice president of global corporate communications at Unilever. 'One of my clients has just taken a three-month sabbatical to backpack around Asia to recharge his batteries.'
Image credit: Gage Skidmore/Flickr