Why do salespeople find it hard to transition into leadership roles?


Over the years, the team at JMA Leadership have coached different people in a variety of industries and in a range of roles. We’ve each of us been either a senior leader or director ourselves. Some of us identify with being a business leader first and leadership and organisational development specialist second.

One thing we’ve noticed is that we’re frequently asked to work with people in sales roles, either:

  1. in a planned way: to help them make the leap from being a successful individual contributor to being a credible people manager, or
  2. because something has gone wrong. A Head of Sales is ‘bringing in the numbers’ but not ‘displaying the right leadership behaviour.’ They’re doing well on the ‘what’ axis, but not on the ‘how.’

The regularity and frequency we’re asked to coach people with a sales background and leadership responsibility has got us thinking.

Why might this be?

What can be done about it?


A combination of the following scenarios plays out at many firms:

  • Top-performing salespeople get promoted to become sales managers, but don’t actually know how to manage. The result is a disaster—productivity takes a dive, disgruntled salespeople start heading for the door, and the new managers themselves burn out
  • A sales leader (read: Head of, Director) has been managing a team for some time, they’ve performed well in terms of targets and specific deliverables, and because of this their leadership behaviour has never been challenged. Things change, things happen and their approach, which has historically been viewed as successful and tacitly allowed, now comes into question.

Sound familiar?


Let’s first of all, take a look at why this might be:

Why are so many salespeople so terrible at leading, coaching others, changing their ways of doing things?

Because even after they put on their manager hats, they often continue to suffer from the “super salesperson syndrome,” unable to disconnect from the thrill of selling. This leads them to hover over their salespeople and micromanage every deal to make sure it closes. *

We see this in other walks of life, not just salespeople in corporate organisations:

  • The super-talented surgeon, who wins great accolades and applause for their scalpel work is promoted to team leader, responsible for other surgeons and their work; yet doesn’t enjoy being away from the bright lights of operating theatre so decides to return
  • The head-teacher who after a few years realises that they loathe the management and administration side of their role and miss being in front of a class of school children.

What does this mean?

It’s about a difference in personal leadership values, which means what do these people value from their work? What do they find meaningful and enjoyable? What brings them credibility? What do they want to be known for?

What has the organisation values and rewarded them for? What is the true expectation of them in their role? What are they measured on, what do they get recognised for?

Ultimately, how do they identify themselves?

Many people never take a moment to sit back and think about this.

Particularly not when they’re offered a promotion and, in their company, the only way to a more senior position, and greater salary, is to take a role that includes a hefty bit of people management.

It’s all about being able to make the shift from valuing oneself and ones’ own output to valuing – and caring about – others and their achievements. Getting things done yourself vs getting things done through and with others.

It’s a big transition that many people can’t make.




Which leads us on to talk about: is it actually just salespeople who have this challenge?

No” is our answer, problems with making the transition happen to people with other backgrounds. We’ve seen it happen for those on career trajectories in risk, accountancy, IT, engineering, operations, marketing. Yet salespeople tend stand out in organisations due to their typically extraverted behaviour. They are the loudest, the problems with their leadership performance are noticed more readily.

The sales department is where a company’s leadership behaviour is frequently in the spotlight. Sales touches on all aspects of the business. Sales is the pounding heart of a company’s cash flow, where the numbers coming in that day, week, or quarter often dictate the direction of the entire operation.

Sales Leaders are outgoing, they’re high profile. They cast a full-sized leadership shadow. How they behave heavily influences – and impacts – organisational culture.


What can be done?

The answer to this problem is not as simple as deciding that high-performing salespeople shouldn’t ever lead. We’ve worked with some amazing Sales Leaders who’ve been able to make this transition. They’ve become outstanding leaders through developing their empathy and EQ skills and through openly acknowledging that they need to show up differently and learning how to through their work with us.

Just like anyone promoted into a leadership role, salespeople must learn how to manage, and sales leaders must learn how to lead.

People who we witness struggling with this tend to have a high need for certainty, for control, they trust the numbers rather than people around them. They prefer the tactical to the strategic, the concrete to the abstract. That’s why the ‘what’ is more important than the ‘how.’

Here are our 5 Tips:

  1. Seek to recruit people who work from a position of leading with others and through others. People who believe that their power as a leader, and the capabilities of the team as a whole, expands when shared with others. (As opposed to people who work from a position of ‘power over’). **


  1. Promote the right people into the right roles. What are the cognitive requirements of the work environment(s) in which they’ll need to be successful? What specific operational and strategic work will they need to be doing? What does ‘good leadership’ look like for a Sales – or IT – Director? How is this changing?


  1. Consider whether a psychometric profile at the transition point will be a useful tool to shed light on both ‘current’ and ‘potential’ preferred work environments. Their stylistic preferences and capabilities. Use one which outlines an indicative timeframe for a person’s readiness to progress from the current to the potential level. Agree what time they have to make the transition to the required set of leadership behaviours.


  1. Be clear about what you’re measuring your leaders on, particularly those who are struggling with this transition. Is it sales deals, EBIT, customer retention, employee engagement? What specifically?


  1. Be clear about the benefits of, and the impact of not, demonstrating exemplary leadership behaviours and performing well in the ‘how’ space of any performance management system.


In our experience whilst there are clear themes, there can often be specific reasons why people (sales or otherwise) find the transition from technical expert to leader challenging. Our executive coaching programmes focus on uncovering the driving forces and limiting factors for each client. We tailor our approach to help everyone navigate successfully through their personal leadership transition.


If you’re interested in learning more about how we do this then call us on + 44 1604 340990 or reach out to us via info@jmaleadership.com.


* According to Harvard Business School’s Frank V. Cespedes, the MBA Class of 1973 Senior Lecturer of Business Administration.

** Brene Brown, Dare to Lead.

Image Source: Harvard Business School Working Knowledge