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Getting into Management: Whats the worst that could happen?

Being a manager is deeply rewarding for folks who love the work of managing. There are few things better than hiring a great team, setting an ambitious goal, and succeeding. Along the way there are opportunities to coach and get people where they want to go. If that sounds like you, it's a great career path to dive into.

But being a manager isn't all rosy. I think it's beneficial to talk about the hard times as well as the rewarding aspects.

There will always be times where the deck is stacked against you, navigating that can be hard, but has its rewards. Where things get really hard is when you have someone on your team that is not aligned with the objectives of the organization. It gets worse.  There are sometimes folks who are actively trying to undermine you and others on the team.

This is the worst that it gets and it can get pretty bad.

I want to be honest in this post, but at the same time, I don't want to single anyone out. Truth is, someone that can be actively harmful in your organization can be a great team player somewhere else. So, for these reasons, I'll talk from my experience but also the experience of folks that I have consulted or have confided in me and try to paint a picture that is accurate but not specific.

Also, I want to state: This is all pretty rare. Every manager with 10+ years of experience has a story here, but it mostly the worst doesn't happen very often.

So, you have a problem. In management, it can be sometimes hard to identify exactly what or who the problem is on the onset. This is when you need to be inquisitive. This is where the trust you have with people really pays dividends: You need to the straight dirt and as the boss, getting that dirt will take trust and confidence.

The worst that it gets is when one person on the team is undermining your leaderships specifically. This comes out in other team members lacking confidence in your leadership. Simple decisions start taking time to put into action. Alignment gets hard. People on the team start following the lead of others on the team, effectively creating tribes with allegiances that break the management structure.

There are a lot of things you can do to work through this, but this post is about how it can go wrong.

There is someone on your team undermining your leadership. You need to start the arduous process of documentation. This takes the form of memos (they can have any format but should be relatively formal with dates, people who received the memo and the subject of the memo). You will need to do a lot of these, and document every interaction you have with the person you feel is misaligned. They should go to HR, if there is HR, or to the CEO/CFO.

The documentation serves as contemporaneous notes for possible future legal action. Not against the other person, but likely against the organization where you could also be named in the legal dispute.

The worst that it gets is you document for months, building out a case for termination. It can take a long time depending on when you inherited the employee, the past feedback the employee has gotten from the organization and the team member's execution of their core responsibilities.

This will weight heavily on you and will take a lot of mental space. Make sure to be taking care of your needs through this process, engaging coaches or a therapist that can help you stay sane.

It gets hardest when an employee is meeting their obligations but they are undermining the overall objectives of the organization, possibly by misdirecting other employees or being adversarial (or political) with their team members. In this case you can't take the "easy way out" and PIP them for lack of performance. In this case, you are going to have to terminate them for cause outside of their core objectives. You need a lot of documentation in this case.

If you have a capable HR team, they can help structure the exit plan for the employee, which often involves severance and and NDA. Outside of an HR team, you're going to have to engage a HR Legal resource to get the paperwork drawn up.

Termination in these cases should always be witnessed by another agent of the company, usually HR but in lieu of HR the CEO, COO or CFO. Sometimes they are quick and sometimes they are contentious. You'll get through it and make sure to not fall into the trap of trying to placate at this stage. The decision is made. Go into these meetings with a script and don't deviate from the script while replying that the decision is final and you wish them the best.

From there, you wait anxiously for the signed severance paperwork and NDA. Once you get that, you are good. If you don't, you can expect a lawyer to contact the firm and at that point it if up to your company's legal representation to figure out a final agreement. Your diligent contemporaneous notes will be your best asset for your legal team.

This is usually where it ends. It can devolve, but people are rational and negotiations work. It's hard when you are in it, but as soon as the employee is out of the picture things get better. You can start focusing on business at hand and be grateful for the battle scars and what you have learned along the way.

Trent Krupp

Currently Head of Product at Impact, a market network serving the entertainment industry. Previously, Head of Revenue at Triplebyte and Hired. Founded an agency in my 20's, sold it to Hired and became employee 5. Recruited for Atomic (VC), Credit Sesame and MakerSights. Helped the founders of recruitment tech startups Shift.org, Terminal and Beacon in the early days.

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