CUTTER CONSULTING GROUP

Challenges In Going From Buddy To Boss

July 9, 2024

I used to get on my soapbox and tell anyone who would listen about how bad of a practice it is to take your top salespeople and move them into a management role.


Not saying it doesn’t get me frustrated when I hear about it happening, but arguing over the merits of it won’t change the practice that is as old as sales (and I know it might seem like a sales team only scenario, but this happens in most companies, with most departments – not just sales).


Identifying the Problem

If it’s happened in your org…now what?


What to do when your top – or top percentile – salesperson is now in charge of a team, and they aren’t doing a good job?


Here are some symptoms that you will see from this Team Lead/Supervisor/Manager:

  • They don’t hold their team accountable to activities or results.
  • They are slow to discipline or put required consequences in place.
  • They may do some of the reps' work for them – data entry, admin/paperwork, etc.
  • They approve requests from their team, even if it goes against company policy.
  • When in doubt, they will side with their team.
  • They could go as far as advocating for them vs. what the company needs/wants.
  • If sales volume is down, they will be quick to point the finger at anything but their team’s actions and effectiveness.


Understanding the Root Cause

It all comes down to this: they are on the side of their salespeople. In their mind, they still identify as a salesperson and they know what it was like to try to sell, hit quota, do everything required in the role (like updating the CRM), and make money. They remember how hard it was to get it all done and how some of the requirements of the job – like regular meetings or updating the CRM – kept them from closing even more sales and making even more money.


There is a part of them that is still in an Us-Versus-Them mode.


Sales vs. Leadership

Sales vs. Processes

Sales vs. Accountability

Sales vs. Meetings

Sales vs. Marketing

Sales vs. Everyone else


Might sound extreme, but I have seen that sentiment to be accurate countless times.


The Challenge of Transitioning from Peer to Manager

If your manager/supervisor isn’t performing AND isn’t following through with the processes the company has developed that they know works, and you hear any sentence that starts with “If only the [Team, Boss, Department, Company] would/wouldn’t do/require/make me/etc.” then they have the above mindset.


When you put a salesperson in charge of other salespeople AND you don’t give them any leadership or management training and coaching, they will default into Salesperson Advocate. Not Company Advocate.


For your manager in the ‘Buddy To Boss’ scenario, where they used to be their peer, an extra layer of complexity is added if they are now leading that same team.


Prior to this job title change, they were salespeople together. Which means a couple of things most likely happened.


First, with their peers, they complained about the same things – the leads, the CRM, the admin tasks, the boss, the rules, the comp plan, the lack of free snacks, etc.


Second, as peers, they had peer-like conversations. Personal stuff. Behind the scenes stuff. After hours, at the bar or club stuff. Social Media friend stuff. The peers know things about the salesperson-turned-manager that made them like them before, but now might find it difficult to respect them as a leader. “I am not going to listen to you tell me what to do after what we did together last month.”


Now do you understand why you are struggling with getting your manager to effectively manage their team the way you think they should be managed and led?


So many dynamics happen that basically set that promoted salesperson to struggle to achieve what the company needs.


It’s not their fault…it’s human nature.


It’s your fault if you haven’t done anything to support them in being effective as a manager and leader.


Solutions and Recommendations

What can you do at this point?


  1. Make sure you have a job description and compensation plan that sets that manager up for success. Are they being held accountable to the same KPI categories that their team are held to?
  2. Have a transparent conversation with them about who they work for and should advocate for (the company), and your expectations of them as a manager.
  3. Get them some leadership training asap.
  4. Then get them a coach (doesn’t have to be a fancy/expensive ‘executive coach’ – but does need to be someone who understands the dynamics they are faced with, and ideally someone from outside the org – so they can vent and share without worry).
  5. If it doesn’t get better, if possible, look at switching them to leading a team they weren’t a part of (so a group that weren’t their peers).


Conclusion

If you aren’t in this situation but are thinking about or needing to promote someone into a management role – take all of the above as a warning and roadmap for setting them up in a way to give the best chance of their success.


And of course – if you find yourself with a manager dynamic like this, let’s talk – I can help you with #1-4.

Not sure where to start?


Want to make sure you fill in all the gaps before things start to change?


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