How to Upskill Your Team (When You Don’t Have Time)

Written by Dave Bailey

Filed under coaching culture management

Manager developing talent of startup employee

The opportunity for startups to grow their own leaders has never been greater.

When your company is scaling, it’s critical to develop your leaders. More staff means more information, more communication, and more people management in general. But with so little time to spare, proactively developing leadership is rarely high on the priority list.

When I started my first company twelve years ago, an advisor told me, ‘You shouldn’t waste time training people . . . just hire someone with experience.’

Times have changed.

Smart companies are now leveraging the growing pool of online training content. And if you’re late to this particular pool party, let me explain what you’re missing.

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Hiring Leaders Is Expensive

You probably believe that your next senior developer or marketer is going to rock up and solve all your leadership problems. But the grass isn’t always greener.

Research from Wharton shows that hired leaders often expect higher compensation, stay around for less time, and receive lower performance evaluations compared to internal promotions. And that’s without even considering how expensive and time-consuming it is to find, interview, hire, and onboard new managers.

That green grass? It’s probably AstroTurf.

But how are you supposed to train your managers when you have no time?

Training Isn’t Necessarily Your Job

A few years ago, I was selling education services to bigger businesses. Sales were low, so I brought it up with my executive coach. After laying out all the issues, it became clear that sales meetings were a big source of stress.

My coach stepped in.

‘I have a challenge for you,’ he said as he took charge of the situation. ‘I want you to take three online sales courses.’

‘Three?’ I replied, slightly taken aback.

‘“Yes, three.’”

I was surprised at the suggestion, but I committed to the challenge, and later that week bought three online sales courses on Udemy. The first two were mediocre, but the third was fantastic. While taking the courses, I made copious notes and applied the concepts to my own situation.

And it paid off. With my new-found confidence, I started enjoying myself in sales meetings, and shortly after, the orders started to come in. Those training courses made all the difference.

And the most interesting part? My coach never took the courses and probably doesn’t even know how to structure sales meetings.

A good leader doesn’t need to have the answers: they just need to identify problems and make sure they are addressed.

How to Prescribe Training to Your Team

Websites such as LinkedIn Learning (formerly and Udemy allow individuals and businesses to access a large and growing pool of management training for as little as $25 per month.

Just a quick search on LinkedIn reveals short courses that address common issues, such as:

Compared to recruiting and retaining, the cost of these courses is peanuts. Professional development has been well-and-truly disrupted and it’s readily available for you and your team.

As a leader, you can leverage this content to fill gaps in your team without actually being the one who fills them. Here are some simple steps you can take:

1) Set expectations for regular training: When you set an expectation upfront that online training is part of the manager’s role, it’s easier to recommend courses later without it seeming personal. For example, you might say to new managers:

  • ‘“If we are to scale, we need to build a culture that creates leaders. We all have areas that we can improve, and so we give all managers a budget for taking online training courses at least 2–3 times a quarter, to fuel their professional development.’”

2) Identify specific development needs: If you have a concern with a particular manager, try to pinpoint which skills they need to develop. Be specific. For example:

  • ‘“They just aren’t senior enough yet.’” (too vague)
  • ‘“They lack the ability to present information concisely.’” (specific) 

3) Discuss skill gaps in conversation: One-on-ones are a good time to discuss personal development. As well as providing feedback on behaviours, you also have time to get a manager’s buy-in by talking through questions like:

  • ‘“Where else does this issue show up?’”
  • ‘“What would be the impact of improving your ability in this area?’”
  • ‘“How might you address this issue?’”
  • ‘“When will you do it?’”
  • ‘“How will you know when it’s addressed?’”

4) Assign a training course: Just like my coach, you might recommend an online training course (or three) in a particular area. For example:

  • ‘“I have a challenge for you. I’d like you to find three online training courses on this topic and take them.’”

5) Get them to teach you what they learned: Setting the expectation that they will teach you what they’ve learned from the training is a great way to make the content stick. You might go one step further and ask them to prepare a 15-minute training session for the leadership team in the next meeting.

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Beyond Individual Training

Individual training can be extremely useful for addressing the development needs of a single employee. However, group training can be just as powerful.

Ten years ago, when I was running my first business, we ran into serious issues with our product development. After a series of missed deadlines, the team was stressed to breaking point and eventually one of my lead designers came to my office with his resignation letter already written.

‘“I want to work somewhere more agile,’” he told me. ‘“We’re operating in the Dark Ages.’”

Not on my watch, I thought — so I hired an Agile coach to lead a two-day training course. I decided that the entire team, including the marketers and customer service reps, should attend.

It turned out to be a turning point for the company. It went far beyond fixing our product development process.

Bringing the team together to learn new skills had a radical impact on motivation. Concepts from the training applied to other areas in unexpected ways, and a new shared language made communication far easier.

Professional Development for Startups

I’ve taken well over 50 online courses now, on topics as diverse as programming, design, product management, sales, marketing, finance, coaching, and more. And all this training has had a major impact on my career.

Nudging your managers into spending a few hours every month on their professional development can increase their effectiveness on the job, and boost team morale. And if you can build stronger leaders in-house, you could end up saving a lot of money later on.

Continue reading about team development: 

Originally published May 11, 2019, last updated Apr 9, 2024

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