management readme

Maxwell Wessel
10 min readSep 30, 2020

Hey there <teamMember>!

Welcome to my management readme. This is your guide to all things relevant to working with Max Wessel.

Every manager is different. Mastering each’s idiosyncrasies can be one of the most successful paths towards building a good working relationship. Like everyone, I have a unique style. My hope in writing this document is that I can make my style a bit more explicit. Consider it a guide to getting the most out of me as we push forward towards delivering a lot of impact.

I also want to state clearly this is not a leadership guide. I try to maintain a very principled approach to leadership. But this is my operating system as a manger. (If you’re interested in learning more about my leadership style and principles, please take a look at this article.) If you read this, you’ll understand how my system boots up in the morning when I have my first cup of coffee. The intention is that knowledge helps you navigate the array!

Preamble: My Management Mission

In an ideal world, we wouldn’t need managers. We would live in self organizing companies where information perfectly flowed from one employee to the next, allowing a single values orientation to guide behaviors and ensure the right collective action is taken. Unfortunately, we’re far from that world. A manager’s job is to bridge that gap. As such, I consider my mission to make team better. The tools at my disposal are communication, time, and conviction.

Investing in communication helps me set a shared mission and establish principles to delegate decisions.

Investing my time in coaching and team development helps me grow the talent that ultimately makes the team work. I have no preconceived notion that I can do any of this alone — in fact, I’m quite clueless most of the time. With time and a willingness to ask questions, my hope is that I can operate in service of the team (and I expect the same in return).

Finally, conviction is the tool I use to do some of the hard stuff; grow the team, allocate resources, and make tough decisions.

But day in and day out — I am optimizing my time and effort to make the team better.

My Management Tools

Alright, so if you buy that I’m working to make the team better, the next question is how.

This brings me to the management tools in my arsenal. In all things, I can’t stress enough that process does not substitute for good sense. As such, I tend to be the person that uses simple tools to frame behaviors. When it comes to working with my team, I’ve got just three that I turn to regularly.

Staff Meetings

Staff meetings are hard to get right and powerful if conducted appropriately. My staff meeting is simple. Once a week, my direct reports will meet. I’ll share context on developments of the last week and focus for the week ahead. We’ll review specific operational metrics. Each team member will come prepared to present the relevant accomplishments and focus for their organization.

It’s a meeting used to ensure everyone is on the same page, that we’re making progress on a regular basis, and that the team recognizes what is important enough to focus on. What is discussed in these rooms also conveys organizational priorities. If calling out upcoming customer meetings is part of the rhythm, you can be darn sure that people will be spending more time with customers. (In my past roles, we’ve called out everything from customers, to product releases, to publications — the subject can change, but it’s the staff meeting that makes this possible).

Weekly 1:1s

Every healthy system needs a heartbeat. For individuals in a professional setting, this is the weekly 1:1. For me, this is a meeting owned by my direct report. Broad information sharing happens in the staff meeting, but tactical issues and strategic topics get escalated in the 1:1. The agenda is created by my direct and the time is protected diligently on my calendar. Why is the agenda set by my directs? Because I am fairly confident that if I need to get a question answered, we will make it happen. I know how easy it is — however — to feel a dearth of opportunity to address other issues. So ensuring that this stays on the agenda is critical.

The day before our 1:1, I will ask that each member of my team shares the agenda items as well as a short update about the week prior. The goal of the written update is to ensure I can ask relevant questions without wasting valuable time together on irrelevant issues. Here, as I mentioned, some tools are better than others — but ultimately, it’s behavior that’s critical. I reserve the right to cancel 1:1s for any meeting insufficiently prepared.

Monthly Reporting
Finally, I believe that transparency and consistency in focus provide the most powerful direction possible to a team. I get this from monthly reporting. On a regular basis, in the same format, with the same metrics, I like to see operational reports from my teams. Typically, these should be written in a manner that can be digested by members of various organizations. When they are delivered at their best, they contain rich, cross functional information and are simultaneously shared with all executive stakeholders. (Not just me.)

These reports should openly acknowledge risks and opportunities. This is not an email calling out all the wonderful things a team would otherwise post superficially on Facebook. This is a thoughtful mechanism to help leaders to assess their operations on a periodic basis. The format, metrics, and timing for these monthly reports will be communicated clearly to the team. (And each of these reports is customized to the team in question based on the metrics most representative of the health of the business.)

I should also say that an unfortunate arrow in my quiver is hours in the day. I work a lot because I love what I do — and am genuinely passionate about the people on our team. I wake up thinking about the team and go to sleep the same way. But I also love eating dinner with my family and disconnecting completely from time to time. And while my hours might be long on certain days, I also respect the boundaries that everyone puts in place. For each of you, know that I’m always a phone call or text message away. Also know that if I send emails or texts on the weekend, I don’t need a response ahead of Monday. (Or at a minimum, if I do, I’ll put it in the title).

My Style

Working effectively with me has a lot to do with an appreciation for my style.

I’m Academic:

Of the first things you’ll notice about me is that I’m a bit academic. I try to take time to formulate an opinion (read: long pauses where I’m thinking, not ignoring you). I ask for the data — and expect that you understand it when it’s presented. At my core, I believe thinking critically is of the most important things we do. Once we take a decision we should act with conviction. But we should think about whether our actions are reversable or not. Where we can backtrack, we should experiment rapidly. Where irreversible we should analyze deeply and take considered action. To work effectively with me in this context, be ready for a lot of questions. If you need time to answer, ask for it. But don’t forget to follow up. For me, dropping the ball on thinking is a quick way to lose trust.

I’m Direct:

One of my favorite sayings about a good team setting is “Safe, but uncomfortable.” If we have shared goals and trust, we should talk about the hard issues. If we’re not challenging one another, we’re not getting to the right outcome. Don’t be afraid. I’ll ask tough questions, but I’ll expect the same. That’s how we get better. In all these contentious conversations, we should be kind and considerate while remaining candid. I’ve been in a lot of situations where leaders drove results through fear. That’s not me — because I want everyone to know that pursuit of excellence is a team responsibility. But don’t misunderstand. I expect speed and I expect excellence. Sometimes people misinterpret kindness for a lack of conviction. If we take a decision as a team, I will be nice and ask for follow up, and expect commitment.

I’m Big-Picture Oriented:

I started my career in management consulting. One of my largest failings was the fact that I fell in love with my models. I would spend countless hours developing complex and elegant financial forecasts. The logic of calculation was impeccable. And ultimately the accuracy was low. One day, a Senior Partner sat me down and explained my obsession had a common name: false precision. It didn’t matter if I had built the most complete logic into my spreadsheet. If I’d embedded the spreadsheet with a variety of assumptions that turned out to be wrong, it was all for naught. Instead, he told me to focus on the two to three key issues that foretold the majority of the result. Since then, I’ve tried always to step back and focus on the big picture. For those of you working with me, I’ll demand you do the same. We have shared goals and one logo on the wall. Every conversation should flow from that stance. We should step back and ask about the broader picture and how our decisions and assumptions fit into this reality. As leaders, if we get caught in the minutia it’s a recipe for falling short of our potential. That’s the part we trust our excellent team to execute against.

I Teach Through Stories:

Clay Christensen would constantly tell people who trekked from all over the world that he had no opinions about their business. What he argued is that he only knew theories. The theory had an opinion when applied correctly in a situation. His job was to convey an understanding of the theory and let other people make decisions. I learned from the best. For people used to receiving commands, this can be irritating. I can come off as long winded in my anecdotes. But I ask that you bear with me through them and try to understand the lesson. I’d rather have shared context for discussing the implication than jump right in and make a recommendation. After all, I could be applying the theory wrong — and if you don’t understand how I am thinking through the recommendation, you’ll never be able to tell me.

All I ask is that you try to understand the purpose and point it out if you don’t. I often think things are clear when they aren’t. And I take no offense when you remind me of that.

I’m Disorganized:

Some people keep meticulous lists and leverage all sorts of management tools. I operate by a series of simple principles and rely on a system of team members to operationalize my office. Please forgive my disorganization. It’s, unfortunately, not an excuse for the same. Like me, if you suffer from this — find a way to systematize staying on top of things. Be structured with our time together. Every time we meet, I will want to give you every available minute — but use it respectfully. I will always be behind on a slew of topics. Please help me manage by preparing for our meetings, by following up on actions, and by working with the team.

My Hot Buttons

Alright — now you know a little more about my style and my tools. Here is the warning section. These are the things that really get on my nerves. I should caveat by reminding you that I’m human like everyone else. I expect a lot of my team and hate disappointment. And unfortunately, when I get disappointed, I have a tendency to limit reliance on folks. So I ask that you be conscious of some of these things which are easy to control.

Meetings. I expect meetings to start on time. I expect pre-reads to go out on time. When pre-work is required, I expect it to be done. In fact, in general, I’ve been told I’m one of the few senior executives that expects to see drafts of documents weeks before they’re due. (I also want those drafts to be complete enough to have a real conversation about). It all stems from the fact that I realize time is the one resource I can’t get any more of — and I hate when it’s wasted. I feel the same for all of you. So as a team, be respectful of one another.

Your brain. Use it. I’ve never found myself on a team with people who weren’t gifted in one capacity or another. My ask is that you think through problems from multiple angles. If facts are knowable, please look them up. If a simple Google search will torpedo your argument, be certain that I will do it while you’re speaking. And know that if you do think critically and make a mistake, I won’t care. It’s not our job to be perfect. It’s our job to leverage our peers to improve our thinking, to attack problems from multiple angles, and to avoid making the same mistake twice. As long as our errors aren’t predictable, I’m in your corner regardless of the result.

Finally, there is just one logo on the wall. Remember that fact. A price of admissions to my team is playing for SAP. This is the most important thing to remember. I want to work in a place where we all trust one another and remember that the enemy is outside the building. And I’m blessed to be at a level where I don’t have to tolerate misbehavior against that fact. So please. Remember that there is just one logo on the wall.

My Promise

Hopefully this gives you some insight into how I operate. My promise is that regardless of all of this — I will care deeply about you, our team, and achieving our goals together. And I hope you can feel that every day.

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Maxwell Wessel

President @ Degreed. Believer in human potential. Repeat founder. Recovering VC. Faculty member. Lucky recipient of great friends, family, and colleagues.