How to manage a move from salesperson to sales leader

There comes a time in every salesperson’s career when you start to think about transitioning away from being a lone wolf individual contributor and pursuing a leadership track. But, this career crossroads requires careful navigation – something I learnt the hard way, and have witnessed others struggle with time and again.

When a high-performing salesperson gets a tap on the shoulder, presented with an opportunity to ‘take the next step’, it seems like a natural progression. It’s so logical, many in this position feel they can’t say no. But, it’s absolutely fine to turn down such an offer – and you should turn it down – if leadership is not right for you, or if it’s not the right time. This requires much soul-searching to determine.

It’s absolutely fine to turn down such an offer – and you should turn it down – if leadership is not right for you.

An ex-colleague of mine is a stand-out individual contributor. He’s such a star performer that he regularly receives job offers for leadership roles, both from his organisation and external companies. Each time, he turns them down. Why? Because he has the EQ and life experience to know that he doesn’t have the make-up, nor desire, to be a strong leader. His self-awareness is admirable and decision perfectly acceptable. Leadership is not the only path, and businesses need to recognise this by providing alternative options to people who don’t want to be leaders but still want to progress in their career. 

The road to sales leadership can be rough

If you’ve done the self reflection and are adamant that leadership is indeed the right course for you, you need to be prepared for some bumps along the way. For most, transitioning from a salesperson to sales leader is an incredibly difficult move to make, one that often requires the need for reinvention.

A great salesperson is the ultimate lone wolf. They follow their instincts, compete internally for resources and stop at nothing to achieve individual performance – they’re trained to do so. It’s what makes them effective at engineering value for customers and, in turn, achieving company results.

But, as soon as you move into leadership you need to rewire these behaviours, because they aren’t traits that make for a great sales leader. Leadership is about success through others. You can’t be selfish anymore, you have to be selfless. For some, this can be a real struggle.

For me, I found myself at this career crossroads many years ago. I was at the height of my individual sales career when the organisation I was with was acquired, providing a natural career juncture. At the same time, I was presented with an opportunity to join a competitor and lead a large sales team for them. Although I lacked leadership experience, I had two critical prerequisites: industry and competitive knowledge. For that, the organisation was willing to take a punt.

Given I knew leadership was something I wanted for my career, it seemed like the right time to dive off the cliff. In hindsight, I was probably too young, and certainly younger than most. I didn’t have the life experience for leadership. I would also come to realise that I knew little about myself. And if I didn’t know who I was, how was I supposed to connect with people and lead others?

I was young, impatient, full of confidence and ready for a new challenge, but I had no idea what was ahead and how long the self-investment would need to last.

I was young, impatient, full of confidence and ready for a new challenge, but I had no idea what was ahead and how long the self-investment would need to last.

Not a week goes by without a ‘young gun’ seeking my advice on when to move into leadership. Many underestimate how much pursuing a sales leadership path is an investment in yourself, in the same way you’d invest in undertaking a university degree. In those first two to three years, when you’re grappling with the concept of leadership, it’s common to take a financial hit because your monetary compensation is now linked to how your team performs. This can be a big shock for individual contributors who are very money-driven, self-motivated and focused on the immediate returns of a top-line revenue goal.

What I wish I knew beforehand

If the transition from salesperson to sales leader isn’t managed correctly, it can prove a disaster – for both the salesperson and the company. In my career, I’ve never seen an individual contributor be offered their old job back once they’ve been promoted to the ranks of leadership then had the realisation that leadership is not right for them.

You need to know that you have the support and backing of the organisation because it’s a heavy lift on both sides.

Nor have I seen anyone make the transition to leadership without a little pain. It’s incredibly hard to rewire your brain, unlearn habits and shift your mindset.

That first year in sales leadership for me was very difficult. But, I was fortunate to have had great leaders and mentors who were willing to invest in me – sending me on all kinds of leadership training – and committed to seeing me succeed.

Here are my five pieces of advice to ensure the transition is as painless as possible:

1. You have to genuinely want to be a leader and know why you want it. Your immediate ambition needs to align with your long-term career plan. Blind ambition is not enough!
2. Be self aware. Before making that step, it’s critical to know what motivates you, what values you’ll remain anchored to regardless of the circumstance and what really makes you tick. Understand your personality type, know how others perceive you, initiate 360-degree feedback and be aware of what you need to work on in order to be a successful leader.
3. Make sure you have strong coaching and mentorship during and post the transition. You need to know that you have the support and backing of your organisation because it’s a heavy lift on both sides. You both need to be committed to and have ownership of the outcome. (If in doubt of the benefits a mentor brings, Tony Hughes’s book The Joshua Principle: Leadership Secrets of RSVPselling is essential reading).
4. Educate yourself. If I were to do the transition over, I would have educated myself a lot more on the virtues of leadership. I was a successful individual contributor and didn’t see the value in reading books on leadership. But, leaders actively invest in their education and progression – individual contributors very rarely do, in my experience.
5. Be willing to stick it out. Finally, if you’re certain leadership is for you, you need to be in it for the long run. It can’t be an interesting six-month experiment. Once you are committed to making the leap and have your organisation's support, you need to have the grit to make it work.

While learning to lead isn’t easy, the world is in dire need of high quality leaders to take up the mantle. So, if you’re being called to a future in leadership (for the right reasons), don’t be afraid to step up.