Having a challenge with your manager is inevitable. Whether you prefer it or not, the person you work directly for will be in the top five of people you communicate with most frequently. We owe it to ourselves (and our sanity) to approach these relationships with thoughtfulness, good intentions, and transparency. Below are some first principles to consider.

Have empathy: If things go well in a technology company, the sales team will generally outpace every other department in growth. It's not uncommon to reach 30-40 people before a single HR person is brought on. This can lead to challenges around promoting internally, hiring externally, or even figuring out the exemplary leadership profile. We have probably all experienced one of the following:

Our peer/friend is now managing us.
A random person is now managing us.
Our manager has changed 2/3/4 times in a matter of months.
Our manager is overwhelmed and dropping the ball on requests.

It's important to remember that it's rarely a deliberate decision to make your life more difficult. Starting from a place of empathy can go a long way, not just in your mental peace but also in how you eventually deliver constructive feedback. Externally hired managers didn't decide not to promote internally, managers with 10+ reports didn't decide to skimp on leadership hiring, and if our peer is managing us, we might very well find ourselves in their shoes one day wishing we had an advocate to help make the transition easier. This isn't to say we shouldn't have high expectations of the people chosen to lead us, just that we should try and appreciate decisions through every lens before coming to a conclusion.

Nip it in the bud: Nothing festers worse on a sales team than an issue with your manager. It quickly spirals from an action they took that displeases you, to a named deficiency of the person, to a larger hypothesis about why they will be unable to ever help you succeed. We can accomplish quite a bit by being prepared, open, and direct about an issue with another person.

Being prepared: Documenting, with evidence, precisely what is happening that is causing you frustration. If nothing else, this exercise helps formulate your thoughts on naming and communicating the challenge you are having with the other person. It's hard for anyone to digest or solve general problems like "I don't feel supported." It's a lot easier to get your point across in the format of "when I did this," "you did this," and "I felt this."
Being open: It's impossible to find solutions if you are unwilling to share your problems. Assuming you've done the work to be prepared, you need to have the courage to enter into what will probably be a difficult conversation. Regardless of how uncomfortable it feels, this is a necessary step to rectify a problem.
Being direct: The worst thing that can happen is you do the work to prepare, muster up the courage to have the conversation, and the person on the receiving end perceives something different than what you wanted to get across. It's essential not to use too much fluff or shy away from the point you need to get across. I've found it easier to be direct in a less formal setting than a conference room table, such as a walking 1/1 or coffee meeting. That may be difficult with remote work, but just something to consider.

Know your last line of defense: If after some time of giving someone the benefit of the doubt and working to communicate your challenges in a productive way, you are still not getting the results you need, it's essential to know who or what your last line of defense is and how to activate it. This will vary by company but can take the form of a skip-level conversation, HR discussion, or anonymous feedback and ratings during a review cycle. Like the point on being prepared, whenever you choose to have this conversation, you will need to bring that next person along for the ride on what has been happening, so having a detailed and documented chain of events to share can get you to a resolution much faster than communicating an issue more generally.

There are great managers and not-so-great managers. What is usually most in our control is how we respond to a situation, and although not guaranteed to provide the desired outcome, you'll know you took the high road.

🤘

RepSushi

First Principles for Resolving Manager Issues