I have seen sales representatives start as a Business Development Representative (BDR), aka lead generator, before being promoted to sales representative and then to sales manager, all, in less than four years. This is the biggest mistake any founder can make. 

“You guys, I'm hungry. I know when my stomach growls there's trouble.” - Chunk

Promoting someone too fast, without giving the person time to develop and acquire experience, can only put that person in a situation of tremendous stress and pressure, and will most likely lead to failure.

“We had our hands on the future, but we blew it to save our own lives… Sorry.” - Mikey

A manager is not born, it is made and promoting a top sales representative can be a terrible mistake even if this person has a high level of experience. This is why you should proceed with caution, patience and reflection. You risk losing the cash cow that you have in your top sales representative, so make sure that they understand that they will no longer be responsible for driving those numbers.

Ask them bluntly:  ‘Are you ok to take a pay cut?’ Because a manager rarely overachieves and hits the commission targets like a top sales representative can, and the slight increase of ‘on target’ earnings (OTE) will never compete with a great sales record.. 

“This is ridiculous. It’s crazy. I feel like I’m babysitting, except I’m not getting paid.” - Stef

Asking the right questions should give you insight into why your superstar salesperson wants to become a sales manager. Let me tell you, ego should not be a reason, so answers like ‘I need to progress in my career or it is the next natural step’ should sound the alarm bell that you are going down the wrong route. However, if the answers you hear are ‘growing at a personal level, willingness to give back and develop others’, then these are the perfect starters to move the conversation to a deeper level and possibly start writing a development plan.  

The question that must be asked is: if I promote you, who will your back up be? This is the question you should always be asking, and as a rule of thumb any successful leader has to be thinking about their replacement to ensure security and growth 

This will give you insight into how seriously your top sales representative has been considering the impact of them stepping into a leadership position. You want someone who demonstrates that they can think strategically, as a team player, for the future success of the team (right answer) rather than a person who is thinking solely about his or her advancement (wrong answer).

“Don’t you guys see? Don’t you realize? He was a pro. He never made it this far. Look how far we’ve come. We’ve got a chance.” - Mikey

Another thing to consider is that people are rarely ready to start from scratch when they’ve been at the top of their game, some warning on the challenging times ahead will be required: stepping into management is like stepping into parenthood: you will require patience, the courage to let them fail and more importantly the ability to be caring and supportive without overstepping.

“Kids suck.” - Mama Fratelli

Such challenges can arise early, in fact as soon as the first quarter when the transition has not settled. Under the pressure of a global team quota, your new manager will probably forget their new role and responsibilities and find themselves acting as the salesperson on the account. 

This, however, should be an immediate warning: a leader should always be there to support the team, not to act on the salesperson’s behalf and this type of attitude should be called out immediately, no matter the pressure of the numbers.

This can translate from smallest actions such as taking a call to actually closing a deal on the rep’s behalf. Educate, teach, use psychology. Put your manager back in the sales rep’s seat. How would they have felt if someone were to get involved in their sale? 

  • Inside tip, they may come up with excuses such as: I was the sales rep on this account, the customer is used to talking to me
  • My sales rep was on vacation 
  • The prospect will only move forward if they talk to me 

Don’t be fooled, act on it, refocus them where they should be, in their new leadership role. 

“Is your mommy here?” - Elgin Perkins

“No, sir. Actually, she’s out at the market buying Pampers for all us kids.” - Brandon Walsh

Now does this mean that you should not give a chance to your best people? The most dedicated one? Of course not! Everyone deserves their own time to grow into a challenging position. 

First assess the situation with a skill/will program. This will combine an evaluation of the capabilities required to successfully achieve in their role (skills) and an evaluation of their motivation and constructive attitude towards the positive impact they can bring(will). 

You can achieve this by asking questions like: How do they rate themselves from one to four in their current role (capability to generate new opportunities, the capability to execute on an account plan, the capability to access the executives at prospects…). Are they consciously competent or unconsciously competent?

Do you believe they can teach, coach and transmit their skills to others or do they believe it is inherent to their own character? How satisfied are they of their current role? Are they eager to move to another role and if so, which? Build a path to their next role. Keep your best people, train them, develop them.

“Don’t you realise? The next time you see the sky, it’ll be over another town. The next time you take a test, it’ll be in some other school. Our parents, they want the best of stuff for us. But right now, they got to do what’s right for them because it’s their time. Their time! Up there! Down here, it’s our time. It’s our time down here.” - Mikey

Now, sometimes you teach, you coach, you give them the right tools and language, but it does not translate well into actions. Your newly promoted manager may try to recruit by trying to clone him/herself, or step into micromanagement or act as a sales representative again.

“Pants and shirts go in the… oh, forget about it. Just throw everything into cardboard boxes. Clark, can you really translate all that?” - Irene Walsh

“For sure, Mrs. Walsh.” - Mouth

“(In Spanish) The marijuana goes in the top drawer. The cocaine and speed go in the second drawer. And the heroin goes in the bottom drawer. Always separate the drugs.” - Mouth 

The best examples of those who have an amazing career as VP of Sales/CRO were promoted by a Mentor who stayed by their side throughout their transition. From Sales to Manager, Manager to Director, Director to VP and so on. You are not born a leader, you are made one by another.

It is not the place of a CEO to promote a sales representative to a leadership position if he cannot provide the mentoring needed for them to learn how to teach, coach, develop, recruit and forecast. 

As a mentor you are preparing your mentee to do as you do, to delegate, trust, build, recruit and more importantly, take assertive decisions. As a mentor, you are backing up your mentee in all their decisions.

As a mentor, you must remember that you were once there yourself, and that, even if your top sales representative was the best, they were also human, learning along with your mentoring and coaching. Forgive and forget, train and develop again.

“I hit the wrong note. I’m not Liberace, you know!” - Andy

Caroline Franczia is a regular columnist for Maddyness and the founder of Uppercut First. Experienced in working for large companies such as Oracle, Computer Associates, and BMC, Caroline also lived in Silicon Valley for four years before moving to startups (Sprinklr, Datadog, Confluent) where she witnessed on the ground the benefits of a well-thought sales strategy. These are the foundations of UF: a structure that accompanies the European startups in their sales strategy by giving them an undeniable advantage in their go-to-market.