Onboard Like a Boss. 3 Ways to Keep Someone Else’s Employee


Few of your teammates officially report to you, but your first few days with a new hire are crucial to ensuring your own success.The way you handle their first days will set the tone for years of success or frustration. Here is how to send your new team member home feeling excited about day 2.

1. I’m Not Your Boss But You’re Worth My Time

Make sure to spend at least two full hours with the new hire. What you do is up to you (take him to lunch), but be sure he knows the most important thing on your agenda began with his name. For legal or personal reasons, an indirect report can tell you things they may not tell their boss. Establish yourself as a sounding board for frustrations and a safe place to send very silly questions.

2. First Swing Home Run

While onboarding, make sure your new team member knows how she can win. Few things are as frustrating as putting in extra effort and having no impact. But if her role is clear then her first project has a chance at being a home run. Put clarity first and worry about micromanagement later.

3. A 10 Minute Rule

Get results for his first questions or requests within 10 minutes. Does he need credentials for the company wiki? Is something on his laptop not working? Set the tone that says “our job is to make sure you have everything you need – NOW” rather than “email that guy you don’t know 3000 miles away and he’ll get back to you in 3 days – read this 400 page manual until then.” A 10 minute target is difficult to hit and can’t persist forever, but you have the chance to set the bar very, very high.

It’s Their Job to Overreact

So say Thank You.

If you work in anything resembling a ‘product team’, you have the responsibility to combine a multitude of perspectives into something resembling a business plan. For this reason, I believe that empathy is one of the most underemphasized qualities necessary for a successful Product Manager (in the Pragmatic sense).

Someone with a more siloed role is paid (not encouraged, but expressly given money and a business card) to treat their perspective as the most important perspective in the business.

So when someone screams ‘the sky is falling’, remember that means they’re awesome.

And say thank you.


Someone Killed My Baby. Turns out it was Me.

I just got an email announcing a project I poured my heart, soul, and midnights into for a few years is being canceled. Or worse, the new idea is being scrapped and the predecessor just got a sorry facelift.  I’ve sinced moved on to bigger and better things, but why couldn’t we change the world?

I read all the books, wrote all the fun Product Manage-y documents, and cheer-lead the team with strident optimism, but it still failed. For everyone who calls themselves a Product Manager, please listen closely.

You need to be tough.

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3 Things I Wish I Knew Before Becoming a Manager

A buddy of mine called me for lunch last week and asked “I’m being promoted. What do I need to know to be a good manager?”

Off the cuff, I responded with the three things I found most useful as a manager of people in Professional America. Here are the bare bones:

1) Daddy Issues

It’s true – when you become a manager, you are instantly the focal point of any and all feelings a person may have toward his or her mother, father, nation, or other authority figure. So don’t take it personally if someone reacts out of character.

Listen quickly and speak slowly, realizing that over-emotional reactions to simple situations mean something else is going on.

People will get mad at you. That’s okay.

2) Your Job is Clarity

As a manager, your job has just changed from doer to decider. No longer do you have the luxury of putting your headphones on and disappearing for 6 hours, delivering an amazing [insert widget here]. Your job is to make sure everyone on your team can disappear and get things done. By clarifying expectations both above (to the CEO) and below (to your direct reports), you replace confusion with confidence.

Push Back. Don’t be a wuss when talking to executives, because if you relay a stupid/unclear/inconsistent idea to your team, you’re the fool. If you find yourself pushing back too much, update your resume and vote with your feet.

Set the stage for your team to be amazing.

3) Treat Everyone Different.

If someone tells you to treat everyone equally, they’re a moron. Treat everyone with equal respect, definitely. But engage with people according to their needs. The situational Leadership tool was great for me (thanks @CameronHerold). 

The basic idea is: 1) Determine how skilled someone is at a given task. 2) Determine their motivation. 3) Combine the two to choose the right style for the project.

But those tools don’t work. Right?

Actually, they do. Even if you only end up talking about it once, the exercise in ‘here’s what I think you need, what do you think you need?’ creates a beneficial forum.

Use your Powers for Good.

Books to read when considering a leadership role:

The One Minute Manager – Read it. It will only take 30 minutes.

Wooden on Leadership: How to Create a Winning Organization – Great insights from the Wizard of Westwood.

The Five Dysfunctions of a Team: A Leadership Fable – How to tell when things are breaking.

Tribal Leadership: Leveraging Natural Groups to Build a Thriving Organization

The 3 Reasons Why Your Agile Project Stinks

With so many small software projects popping up, “Agile” project management is all the rage. But your specific Agile project is doomed, because you’re clueless. Here’s why.

1) Tools and Discipline are Different

Let’s use Trello. Or Excel. Or Rally. Or Pivotal Tracker. Or Jira’s Greenhopper. I know, let’s use all of them!

The tool you choose to organize your project matters much less than the discipline you bring to the tool. If you populate the tool with horrible user stories, you lose. If engineers don’t update the tool, you lose. If the meetings around the tools don’t run well, you’ve just lost your audience (and your credibility).

Your Trello board needs to flow from Left to Right – it’s primary visual value.

How to know if your discipline is right: Check your email. Are there more than zero messages in your inbox? Chances are your discipline needs work. Email with discipline is one of the best Get Things Done tools in the world. Without discipline, it’s a black hole of loose ends prioritized by recency, emergency, and your highly caffeinated recollection of other highly caffeinated moments.

Bring discipline to how you use your tools and you’ll find their limits rather than your own.

2) Thinking (and Math) Still Required

Agile Project Management is a tool set that has grown from other tool sets. Each of these has been highly tuned to the needs of its context. Lean, Six Sigma, Kanban, TQM, Waterfall – densely packed terms meant to solve specific situations. Software has specific constraints, and different software environments have their own nuances. Are you deploying to a large datacenter? Agile doesn’t make hardware procurement and setup (a very serialized process) very easy.

Take the time to understand why a certain tool is supposed to work and help your team understand it. In other words, Learn the Math about why these small, independently valuable, estimable, testable things result in more cool stuff for your customers.

This book is not about Agile at all, but it’s why Agile works.

I’ve seen Scrum Masters literally reduced to tears because they couldn’t convince an engineer that the Agile way was a better way. If they had read Reinertsen they would have chosen different battles and had a clear understanding of why the next step was the most logical one.

 3) You’re Not Big

Most literature about Agile projects take the perspective of a big company. The big company needs to change, so they do Agile things to streamline their product management overhead, reduce their silly assumptions, and win. For them, Agile is a change away from too much structure, and the engineers rejoice.

But your developers aren’t being liberated and don’t love this idea, because Agile tools are increasing their overhead. Why do I have to drag this box? Why do I have to estimate how long this will take? Break down the project into smaller pieces? If your team has to ask why too many times, they begin to say no by default. And they should, because you’re very likely dumb.

Grow Your Project: Instead of showing people an empty burndown chart and expecting them to not freak out about your new Big Brother ways, start with the simple tools and grow structure as more structure becomes valuable.

Take the time to understand before you seek to be understood. Your team really would rather be high performing programming ninjas, so make sure your new collaboration-based approach starts with a highly qualified individual – you.

You are an Ironman.

I just finished my first Iron distance triathlon. I tend to get emotional when I think about race day, so I’m going to keep this as structured as possible.


I was a mess. I had a good face on, of course, but I really wanted to finish. It was nine months of training weekends, physical therapy, and a life transformation, all for one event. Most of my family couldn’t make it for financial reasons. My dad couldn’t come because his brain cancer had reared its head the week prior, barring him from flying. The girlfriend I had at the beginning of training had recently been lost. I told a supportive ex that I couldn’t have her come cheer.

There was a lot going on in my head, but loudest of all was this:

        I feel sorry for whoever tries to take me off the course.

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