I’ll be giving a talk at BadCamp called “Mistakes I have Made: Collected Project Management Failures.” It’ll be funny, and true, and probably reference a few different stories from the past. However, when I look at what the real truth is to a talk about project management mistakes, I go to the source. What are the hardest things about project management?

If you google this, you’re likely to get the answer of ‘everything’.

For me, when I look at this, I separate this out into five different areas of hard:

1. Team
2. Clients
3. Services
4. Alignment / Mission  
5. General Sucking: Hard decisions

1. Team

Around the area of team, I think this is one of the biggest things that you’re hired to watch over as a project manager. It’s your job to make sure that you’re engaging the team to make sure that the problems get solved, that you’re building what you set out to build. It’s so common in my own work that when I feel like there is friction or struggle, I have to lean back and ask myself if I’ve actually worked on really engaging the team – or if I’ve just charged ahead full bore.  (Mistake #543)

Do I have the right team?

I have definitely been on projects or working with teams that just didn’t have the right fit. There had never been a conversation about if the people working on that particular ‘thing’ were right for it. (Mistake #324) Or they were being used in ways that didn’t suit them personally, they were being asked to use their weakest skills in a really strong way, and it was burning them out. (Mistake #221)

Did I give everyone enough time?

This is where people will use Agile to its best advantage. Agile, when you’re actually tracking story points and estimating, will give you enough space to be able to understand if you’ve crammed too much in. (Mistake #112) Did we ask too much in that space from people? (Mistake #14) Are we working under a really silly timeline (Mistake #87) and did we not find out until too late? (Mistake #98.) Even more to the point, once we know the problem, are we not willing to correct it? (Mistake #465)

2. Clients

Do we have the right clients? Are we, the people building things for them, the right people to do it? Do we understand their mission? Did we do enough to make sure they understood when, how, and where we were going to build? Do they understand what we’re not doing? Are they ok with their role here? Do they understand ‘scarcity’ in action? Does that shock them?

The list goes on, but in order to be the best technology partner, and you’re helping to lead everything to the finish line, everyone has to agree.

3. Services

This is the day-to-day stuff and where new project managers that are client facing get tripped up. Answering for the developers when you shouldn’t. “That should be easy.” Making estimates with having no idea what you’re doing. Estimating things in general. Making the expectations that you’re going to be available all the time. Or not setting the expectations at all.

Services isn’t the hardest-hardest part of this, but it generally adds to it.

4. Alignment / Mission

There’s a statement running around the internet right now that working on things that aren’t aligned with your values is just stressful. Working on things that are is called passion. You’ll notice when it’s just not working, because you can’t get rid of that pit in your stomach, that sinking feeling. Not listening to it is a big mistake.

5. General Sucking: Hard decisions

Part of your job is being the person that says no, that continually tries to find a way to make the project a success. You’ll sometimes be in the place where everything, all of these 4 things above are collapsing around you. And it sucks. And it happens to a lot of us that do this, because you are the one that’s pulling the threads together.

It gets better.

You are not always going to have these weeks. I refer to them as ‘hell weeks’. Please keep your hands and arms inside the hell week until it comes to a full and complete stop. In these weeks, it’s even more important for you to pay attention to you. Get some sleep. If you can’t get some sleep, talk to your team about how you are feeling, and figure out how to articulate what the problem is so that everyone can solve it together. (Also, ask yourself how you’re working with your team!)

Internalize the idea that you are no good to us dead, and take care of what you can. Projects end, one way or another, and you’ll get through it – one email, one day at a time. These things are hard, projects are hard, building things is hard – but hard things are worth doing.

Hope to see you at BADCamp for my session “Mistakes I have Made: Collected Project Management Failures.” Check out all of the Phase2 thought leaders at BADCamp!