Hiring, training, and letting go of project leads

Issue 3 of 5: When to train

This is the third instalment of our mini-series on Training vs letting go of project leads.

Issue 1: The cold, hard facts
Issue 2: When to hire
Issue 3: When to train
Issue 4: When not to train
Issue 5: When to let them go

Let’s dig in:


Last week, I shared the slurp on when it makes sense to hire. It’s vital to hire your project leads when you observe initial processes faltering at between 5–10 people and you should keep hiring a new one for every 5–10 folks added.

This week, I’ll rip open the soup packet and drop the broth re: when it makes sense to train your project leads (whether you call them AMs/PMs/Producers/DPMs or Great Odin’s Ravens).

There is a distinct moment in my early career as a digital project lead that still gives me palm sweats when I think about it. I had worked with a great developer to estimate some geolocation filtering and tagging on a marketing site and the build turned out to be much more complex than we had initially scoped. I was terrified to explain to my boss and to our clients why we were about to go over budget by thousands of dollars and I remember experiencing the bloating discomfort of unconscious incompetence poking me in the bowels (I sure as hell didn’t know what I didn’t know at that moment).

What I didn’t know

I didn’t know how to spot the red flags before they bit me in the ass. I didn’t know how to ask our dev the right questions about how the CMS would access or render the data. I didn’t know it was okay to tell my client that increased complexity is unpredictable and yet completely expected and that this complexity meant we needed to take more time to get it right—aka it would cost more and it was okay to charge them for it so long as they knew how it impacted the project and delivery and they signed off on it. I didn’t know how to renegotiate the change in the budget—I just hoped our dev could work faster. I didn’t know how this drag would impact our cash flow and client profitability. I didn’t know what data was important or which metrics to keep an eye on. I didn’t know how to react or process my stress because I didn’t have any peers in the industry to confide in. I didn’t know how to ask for support from my boss because I felt guilty for fucking up. I didn’t have a plan to fix things because I thought I was the problem.

I didn’t know any other way to be a project lead.

Let me shout this at full volume: I never ever want any project lead to feel the way I felt in that moment. To feel the fear and loneliness of carrying a doomed or mutilated project on your shoulders and bowing under its weight because you don’t know how to make it healthy again. It’s a shaming and terrifying experience when you can’t navigate your surroundings and you don’t know where the fence posts are. It’s overwhelming to be responsible for the success of a project worth hundreds of thousands of dollars when you don’t even know what its sillouette looks like. Or how to ask for help or what normal even looks like when you feel like you’re standing alone in the ring fighting against the ‘we just added it because it looks better’ creative pushback. A project environment can be a disheartening and lonely place. It can be an infinitely complex and difficult space. But it doesn’t have to be. And that is why we made this apprenticeship program.

Why train? This is why.

Here are some solid reasons to train your project leads.

In this industry, there are no standards (yet). Training provides a framework for project and company health.

Most project leads don’t have formal training for the digital world. Traditional certificates are for bridge building and mining projects and focus primarily on hard skills. Proper training should prepare your project leads how to tie project budgets back to company profitability—not just how to time track against an estimate. How and when to say yes, maybe, no, later, and how each of these responses has its own intrinsic power to change outcomes and balance risk. How to support and be allies to their project teams and points of contact so they come back again and again. How to take up the space they were literally hired to stand in.

They need a community and to be surrounded with support

Project management is a lonely career. There is often a 1:4 or 5 ratio of project leads to teammates, and they tend to work in siloed environments. Plus, their work is usually invisible or underappreciated as part of an ‘administrative load.’ Training gives project leads a connection to other folks experiencing the same pain points, elicits empathy, and injects their day with new ideas they can bring back to the team. Instead of cold gut thumping project anxiety, they can share a tall drink of project kinship.

It gives them a reason to stay and grow with you

I’d bet that if your project lead is juggling more than five projects and there’s no clear growth path within your company, they have at least one eye on the door waiting for the next lateral raise with some other company. Training gives your project leads a chance to plan their future with you. When you invest in them, they invest in your company. Not only that, it is expensive to replace candidates when they leave (anywhere from 20%-40% of a new hire’s salary). So it’s a smart investment.

It’s cheaper to train than to hire

It’s more affordable to train a candidate than to search for a "senior" level candidate (years of experience can also mean years of bad habits). Do the math: senior level digital project leads cost anywhere between $80–120K/year to keep. Midlevels with training cost $60-90K, they aren’t yet jaded and can attune to your organization’s processes in nearly as much time as it takes to fully onboard a senior. Plus, if training is tied to promotions and salary bumps, it incentivizes their commitment to stay.

Okay, you know why you should train them, but how do you know when?

When to train your leads

Here is when to think about training your leads:

  • Promoting a great junior or mid-level: If you’re rounding out your team and have great junior candidates with strategic brains, solid affinity for people quirks, and a need project management structures and strategies, training can set them up for a strong leadership path early on (plus, it’s super cost effective).
  • Rewiring bad habits: If you’ve got a self-taught project lead who’s picked up a few bad habits, wants to be more strategic or build their soft skills, training can provide a non-judgemental way to encourage new ways of thinking about old processes and practical tips for applying them.
  • Deepening related skills: If you’ve got awesome office managers, coordinators, and administrative folks who light up the room and automate processes naturally, and you see huge potential when promoting them, training can elevate them into a new career path or management role they might not have considered.
  • Rounding out those T-shaped skills: If you have fantastic designers, content writers, UXers, or developers who are naturally good at communication and leadership and want to lead projects and teams, training can help them build their autonomy to lead projects with leaner processes while deepening their business understanding.
  • Galvanizing the team: If your team is highly autonomous and wants to roll out operational or project management changes in tandem while on the same learning trajectory, you can put them through training together and sit back as the jet takes off.

Myths about training

Let’s bust a few myths on our way out, shall we?

They’ll just leave

You’re afraid if you train people, they’ll just leave: that’s false—people are much more likely to stay when you create a learning organization and a safe cultural environment where they can grow and develop (that’s your half of the commitment). 85% of our candidates are still at their organizations a year after training is over. The ones who don’t stay often leave because they face untenable roadblocks or resistance to change. We train them to better the organization, not just themselves. It’s also better than the alternative: you don’t train them, and they stay.

We don’t have time

You don’t have time to stop the frantic pace at which you’re processing work and chewing through employees? Or you don’t have time to build in strategic focus to work on the business as well as in it? Both? You have time. In fact, training gives you time back in the form of better strategic planning, deeper focus, and it lets you trust that your project leads will do their jobs, so you can do yours.

They’re already good enough

Learning and professional development starts with your project leads, but has a ripple effect that impacts the entire organization. It affects how they relate to their teammates, how they process stress, and how they prioritize what’s important in their lives. Training lets your leads reflect on what they’re already doing a good job at while embracing lifelong learning in new or unfamiliar territory. Then they can begin to teach that knowledge back to the team.

It’s too expensive

Erm, nope. Good training for project leads yields significant returns back to your organization in the form of additional revenue and profit, lower team turnover, smoother launches, and longer engagements with clients.

Bam. You know when to train. What’s next?

Up next

Keep your peepers on your inbox. Next week we’ll be covering when NOT to train project leads.