Building the boat while sailing it - Getting started as a new project manager

05 Dec 2021

High-performing individual contributors are often promoted into management without prior experience. They’ve built a reputation as fast learners, and they’re expected to pick up the skills on the job.

Fortunately, there are thousands of great lessons on the internet. You can read up on running effective meetings, identifying your critical paths, handling conflict, and everything else you need to succeed in your new role. On the other side of hundreds of books, blog posts, videos, and podcasts, you’ll fill your head with enough information to pattern-match your challenges to existing concepts. With enough experience, you’ll do well.

Unfortunately, you just inherited a new project and team. It’ll take you months to absorb enough literature to get up to speed, but your team needs you to act today.

What do you do?

I’d like to answer this question today. I’ve been lucky to be in a position to help multiple new project managers get up to speed and have seen that day-one “everything’s on fire” stress many times. You’ve just been giving the blueprint to a boat and are being asked to build and sail it at the same time.

I will propose a methodology to get up to speed without blocking your team. First, we need to get you in the right mindset. Second, we need to work through your first day. Finally, we need to get you building the boat while sailing it through a healthy blend of doing and learning.

Let’s get started.

Your mindset

As a new manager, you may already be letting the title go to your head. You were promoted! You have direct reports! People around you are saying business jargon! Surely, you’re on the right track.

You should be proud of yourself, but let’s slow it down. Take a deep breath and think through what you’re now expected to do.

As a manager, you no longer do real work. Instead, you are relying on your team to get things done. Your job is to make your team as effective as possible by taking everything off their plate that’s blocking their ability to be productive.

Your job is to be a servant.

Are your team members unable to get into deep work due to too many distractions? Find ways to get each of your team members unblocked chunks of time.

Move meetings to the ends of the day, keep meetings structured, take on the bureaucratic paperwork, and manage external communication. Do the rote work so your team can focus on the hard problems.

You must be a stress absorber.

Is your client asking to change the targets? Are you burning through your money? Are other projects demanding more time from key team members?

Handle these issues.

Keep your team apprised of anything that might affect their ability to perform, but do not reflect or amplify your stress. Instead, turn stress into a prioritized to-do list.

You must be honest.

Do not hide bad results from your clients. Do not present an artificially rosy picture to avoid conflict with your team or other stakeholders. Do not avoid difficult conversations.

As you get up to speed, you will read plenty of great articles on managing conflict. These will help hone your skills. However, honesty is a mindset and something you can start practicing today.

You must be organized.

As you get more experienced as a manager, you’ll learn lots of jargon. You’ll find a near-bottomless list of methodologies and software options, all purporting to be solutions to the challenges you’re facing.

Software may help you one day. You’ll move from spreadsheets to Asana💬or Jira or Wrike or Trello or Monday or ClickUp or SmartSheets or… and you’ll be Kanbanning💬or Waterfalling or Scrumming or being Agile or… with the best of them.

However, the improvements brought on by frameworks and software are just that. Improvements. They’re not going to make or break you.

Look around you. What is everyone on your team doing? Why are they doing it? What needs to be done? As a manager, your team is looking to you to break down complex targets into actionable to-do lists.

A well-thought-out to-do list on a piece of paper will beat out a disorganized plan loaded into expensive project management software. Every time.

Your first day

It’s now day one. You know your job is to serve. You need to absorb stress, be honest in the face of conflict, and stay organized. Great. So, what exactly do you do?

Your first priority is to show your team that you’ll be their rock. You’ll do that through a project kickoff meeting.

Discuss the big picture

Why is this project important to the company and the world? What’s the context behind the technology you’re developing, and why is it a big deal? Get your team excited about what they’re working on while showing others you deeply understand the big picture.

Talk through your work plan

This is the time to confirm buy-in from everyone on your project team. Make sure everyone knows what they are doing and why they are doing it.

This can be done through any jargon you’d like: deliverables, milestones, plan, roles, budget management, etc. How you present doesn’t matter. What matters is that the team is on the same page.

Make sure there’s complete agreement on these high-level items, as they’ll become core as the project expands from idea to execution.

Get buy-in on a high-level schedule

A project kickoff is a commitment to turn time and money into a deliverable. Make sure your team is bought in that the deliverable is achievable with the allotted time and money.

If your team is not bought in, it’s already time to prove your worth as a manager. Be a servant. Listen to the issues, catalog them, and bring them up with your client. Next, be honest. Tell your client why your team is concerned. Your client may cancel the project💬This doesn’t look good, but it still looks better than picking up the pieces of a failed project months from now. but they may also be willing to adjust their plans. Most likely, they’ll acknowledge the issues and ask to proceed anyway. This provides a clean conscience for your team and an opening to negotiate changes down the road.

Plan your immediate priorities

Ignore all the project management concepts you may or may not know. Grab your favorite writing tool and make a list to answer this question: what are the most important tasks to get done today? What needs to get done first, and who’s responsible for getting it done?

Present it. Make sure everyone leaves the meeting knowing exactly what they need to do.

Giving your team a list of immediate priorities will provide you with breathing room for the next stage.

Protecting your most valuable resource!

As you get into managing your project, you will come to recognize that time is, by far, your most valuable resource. There are plenty of high-quality learning materials on this topic, but there’s an important stumbling block to talk about today: the post-kickoff meeting slump.

With the team organized, money in the bank account, and months to years ahead, everything’s looking great. Without focus, project teams will squander these early weeks with ineffective prioritization and needless work. You’ll be kicking yourself a year from now when everything feels like it’s on fire.

From day one, set the tone by providing a list of prioritized tasks and owners. Continually prioritize, and always treat time as your most valuable resource even when it doesn’t feel like it is. It will be one day.

Building the boat while sailing it

You’re in the right mindset, and you’ve bought a little time with your team. They’re off and running, but they’re still going to look to you whenever issues arise. What next?

You need to build the boat while sailing it. You need to split your time between learning and doing, and you need to get that split right. Too much learning, and you won’t be there when your team needs you. Too much doing, and you’ll reinforce bad practices and sow doubt in your abilities.

First, remember to be honest with your team. Tell them that you’re learning and would appreciate honest feedback in return. Ask them for advice whenever an opportunity arises.

Second, you need to be organized. Set a schedule for yourself that includes both learning and doing.

The best way to do this is to set routines for yourself. These routines will make you think about items outside your short-term to-do list. Particularly, we’ll think about:

  1. Big-picture schedules. How do your team’s tasks fit into the big picture? Has the definition of project success changed? Does it need revising?
  2. Small-picture tasks. How do you ensure everyone is always working on the highest priority tasks? How do you ensure buy-in instead of quiet disagreement?
  3. Budget management. How do you adjust the spending rate if it’s too high or too low? How do you handle unforeseen budgetary changes?
  4. Learning. Always make time to learn, even when things feel too busy. Even 15 minutes per day will add up over months of management.

Daily

When you get into the office each day, what should you do for your team?

Talk with your team.💬This can be a stand-up meeting, one-on-one meetings, or even Slack chats. What matters is that you’re talking. Make sure they all know their priority for the day and how it fits into the bigger picture.

Unblock your team. Is anyone on your team stuck due to something outside of their control? Are they waiting for a shipment, a legal agreement, etc.? Is someone working on a lower-priority task that could instead be helping out a bottlenecked task? Would getting help from outside the project team greatly simplify a problem? Solve these challenges so your team can focus on their work.

Review your to-do list. Make sure it makes sense, has a person and due date attached, and reflects what the team is doing.

Take the bureaucratic load off your team. Does a piece of equipment need to be ordered? Is there a technical report coming up? Do you need to talk to a third party? Per Maker vs. Manager, you should do everything in your power to absorb the desk work and meetings so your team gets as many unblocked chunks of time as possible.

Learn! Once your team is up and running for the day, sit down and browse through learning materials (more on this below). Read something that speaks to you, as these posts are most effective once you have relatable experience. I spent ~15 minutes on this and then shut it down for the day.

Weekly

Being a project manager is much more than assigning tasks and interpreting results. To be an effective manager, you must make sure you address long-range goals that fall through the cracks when you’re too zoomed in. This is what weekly and monthly patterns are for.

Host a huddle. Get together with your technical team💬Keep it as small as possible! and talk about your work. What did you learn? What would you have done differently knowing what you know now? What’s next? Talk through what you think the next project priorities are, solicit feedback, and divvy up the work💬Even if you have formal decision authority, remember that you are a servant. You should aim to almost never use your formal authority. Convince, don’t tell..

Review project tasks and predict bottlenecks. Versus the daily review, use this weekly review to reflect on how your assigned tasks drive toward the next milestone. De-prioritize paths that aren’t panning out, start-up new ones if needed, and make sure all the paths people are on truly matter for the upcoming milestone.

Finally, remember to get the minutiae done. These are usually expense reports, status updates, and external presentations. Take the lead here so your team can focus on real work.

Monthly

Review your budget. As discussed in Getting things done without setting money on fire, your budget is an excellent metric for identifying issues before they arise. If your spending is not where you’d expect it to be, adjust your project. If your budget is not enough to keep the project going, have an honest conversation with your funders as early as possible.

Host a steering committee meeting. Get your executives together and talk honestly about progress to date. Remember to have the hard conversations as early as possible!💬The biggest challenge I see with new project managers is the tendency to avoid hard conversations. The project will be all green checkmarks until right before the final due date. Everything then turns to red X’s, everyone starts pointing fingers, and things fall apart. Don’t let this be you!

There are hundreds of posts on steering committee meetings and how to manage stakeholders. I recommend starting simple: one slide with red/yellow/green stating how the project is doing technically, on timeline, and on budget. Then, tell the steering committee what they can be doing to help.💬Avoid the urge to make these meetings into 50-slide slogs showing all the great work your team has done. Keep it focused on 1. how it’s going and 2. what can the people in your room be doing to help.

At Milestones

When going into a meeting around a key milestone, be sure you’re organized and prepared. Have an extra-nice presentation focused on the big picture. If you want the project to continue, be ready to defend against people who’d rather use the money elsewhere. If you believe the project should stop, have the courage to say so.

Project Close

This usually corresponds to a milestone meeting. Expect to write an extra-nice final report and distribute this across a broader team. Saving you a ton of management book reading - resist the urge to embellish your team’s accomplishments and instead strive for complete honesty. It’s harder to do but will garner reputational goodwill that will pay off in the long run.

Learning

Project management is not hard; it’s heuristics and best practices.

However, I’ve found that many technical people💬including myself! don’t give any time to the “easy” stuff. If it’s not solving coupled partial differential equations💬in a Laplacian space projected onto an imaginary n-sphere written needlessly with the hardest-to-draw greek letters…, then many of us assume it’s not worth any of our time. However, it’s clearly worth some of our time.

Being aware of your biases is the first step toward learning. The next step is finding a way to learn that matches high information density with your ability to retain it.

In my opinion, management books are usually low information density and low retention. If your brain is wired like mine, you need something denser.

What has worked for me are blog posts and podcasts. Blog posts are great for your morning coffee or awkward downtime between meetings, and podcasts are ideal for working out or commuting.

Next, what has worked for me is finding posts or podcasts that I find relatable at that exact time. Do you have a perceived low performer on your team? Read up on that. Do you have a challenging boss? Listen to a podcast on it.

Read a post or two but don’t binge it. If you’re like me, you won’t learn these softer topics the same way you’d learn a new scientific field. Once you find yourself zoning out, stop for the day. Don’t be ashamed if you zone out in under 15 minutes. Keep at it, and you’ll improve over time.

For where to learn from, try things out and see what sticks. Here are a few options that worked for me when I was getting up to speed:

Finally, I’d like to leave you with a slightly philosophical note on how to view project management.

Project management is like safety, security, quality, and other compliance functions. In safety, paperwork forces us to think about what we’re doing and prioritize in a semi-quantitative way. Just like safety, project management processes are about forcing you (the manager) to think through and prioritize your blind spots.

Like all compliance, project management standards are good when every bit of documentation makes you stop and think. Also, like all compliance, project management standards will tend to degrade into a bureaucratic process with meaningless paperwork.

As you learn, resist the urge to implement every piece of new terminology you come across. Do the opposite. Do everything you can to strip terminology and remove dead processes. If a hyped-up bit of jargon is not improving your project, please stop using it.

If you get in the right mindset and manage to build the boat as you sail it, you’re going to be a great manager. Expect bumps in the road but remember to absorb the stress and continually look out for your team.

Transitioning to management is a fun ride with rapid growth. Buckle up and get excited for your new role!