Motivate Your Team by Taking an Active Interest in Their Future Plans

Money will get people to show up for work and do it adequately enough to not get fired. To get people to go beyond that, you need to help them see their work in the context of their long term goals and committing to their growth.

This post comes with significant amounts of extra dog!

Motivation — it’s the one thing all knowledge-based work companies are trying to figure out. Most seem to have figured out that it’s what sets apart teams delivering superior products and solutions from those cranking out mediocrity, but very few have cracked the code of how it is created.

Some companies try to buy their way in: throw more cash at people and they will soar. Others think motivation is a function of how loud they yell at people.

Some try the route of ping pong tables, chocolate fountains, weekly laser tag outings and complimentary exotic treats.

All this, while their employees are spending their days thinking about something else: their personal hopes, dreams and goals. They are thinking about “what am I going to be when I grow up?” — even the ones who arguably already have.

Funnily enough, very few companies seem to really be clued into this.

“I wonder if chasing squirrels is more rewarding a few yards over…”, Barney thought to himself

Careers Ain’t What They Used to Be

In the days of yore, the dream was that you got a job right out of college, put in your hard 8 hours every day, and retired at 60-something as a happy old person.

That hasn’t been the case in ages. The average tenures of workers in the tech space is well below even the national overall average of 4.7 years, clocking in between a mere 12–24 months for most tech giants.

In the recent Stack Overflow 2017 Developer Survey, only 24.8% of developers listed their job search status as “I am not interested in new job opportunities.

A whopping 62.1% listed their status as “I’m not actively looking, but I am open to new opportunities.

People change jobs every few years. 
This is fine.

Why, then, do most companies have HR and management practices that seem to center around the concept of retaining employees until the bitter end of humanity? Why is the thought of people moving on every now and then so tabu, if it’s the norm?

People change jobs frequently for a few reasons.

First off: they can. Tech jobs are a sellers market. I can throw a rock out of a window of our Empire State Building office’s window and it’ll land on a company starving for talented designers, developers, product people and other talent. Any person a company should be looking to retain has an abundance of options. All of your talent is receiving multiple recruitment emails per week and I can guarantee you they are curious.

Second: it’s by far the best way to make a career move.

When getting bogged down by legacy issues and bureaucracy at your current company closes the path of advancement from in front of you, the easiest way to make a step forward is changing lanes.

Careers goals also change just like your product roadmaps do. The 2-ish year tenure at a company is roughly akin to a sprint in your product development process. Sometimes you need to shift your next sprint’s priorities to accommodate your changed goals.

What if we could just collectively acknowledge the first reason and harness the power of the second one?

Paw-trolman Ruffles reporting for his tour of duty, SIR!

Tours of Duty

My favorite approach to this is outlined in the book The Alliance: Managing Talent in the Networked Age by Reid Hoffman, one of the founders of LinkedIn and prominent tech investor.

While I strongly recommend the full book, you can get the gist in his own article on LinkedIn or this Harvard Business Review article.

What this framework essentially lays out is a mutual contract between employers and employees for Agile career development.

Instead of welcoming new employees with a misguided default expectation of a lifetime of service, both parties acknowledge the finite nature of the relationship.

Once that’s established, the goal no longer is permanence, it’s the maximization of the mutual impact of the relationship.

What can the company do for you, balanced with what can you do for the company.

A Tour of Duty is essentially a 2-year (or whatever time you see fit) sprint where the manager and employee agree on a mutual scope: what impact is the employee meant to have and what skills are they expected to build in doing so.

Once a Tour of Duty is completed, the company and employee can choose to continue the relationship with additional tours, or go their separate ways. No harm, no foul either way.

As long as the duration of the tour has been as mutually impactful as possible, everyone should is happy.

Uh-oh, there comes HR with a powerpoint… and I don’t think it’s about sniffing butts.

Respect is a Two-Way Street

If you’re hesitant to jump all the way in to something as radical as the Tours of Duty framework, there are ways to inch your way in. Some of them may already be in your HR department’s toolbox, but you’ve just never taken them seriously.

I’ll use a dirty phrase: Career Development Discussion.

Most of you will shudder upon reading this. Mostly because it’s oh-so-god-damned boring. But probably also because you’ve engaged in one that was an absolute waste of your time.

Either you experienced it as an employee in the form of a reluctant boss forcing 30 minutes into your schedule to awkwardly talk about “your career”, when in fact you were mainly just talking about that one time you had a disagreement with Bob in the UX team and your boss had to mediate — While your boss fiddles with their laptop because there’s some urgent fire drill going on.

Or if you’re a manager, you’ve probably sat through some boring .pptx-hurricane mandated by HR on the importance of career development as a means of employee engagement, followed by mandatory sessions with all of your direct reports. Next thing you know you’re the reluctant manager in the scenario above, talking about Bob in the UX team, flicking through Facebook while the other person speaks.

What if I told you that HR was right all along and this was a really meaningful thing to take seriously? That you’re wasting really valuable potential.

What if it was actually a skeleton key to motivation?

My passion is this ball, what’s yours?

Find and Nurture Their Passions

I can guarantee you, none of your direct reports are in their dream jobs. Or if they are, I should be reading your blog, not the other way around.

Your entire team is dreaming of something bigger. Something more.

Your job as their boss is to figure out what that is. When you talk to them about where they want to be in 5–10 years and their answer gravitates to something in your current company, immediately call them out on it and tell them to answer again, but take the current employer out of the picture.

There’s an overwhelmingly high likelihood that neither of you will be working at the same company in 5–10 years, so why on earth would they box their hopes and dreams that way?

Once you clear that up and you can start talking honestly and transparently about where they want to get to in the long run, you can really get to business: why are they in their current job, and what can they really get out of it on their path towards their real long term goal?

I guarantee you will find yourself surprised. For every person that is actually on a linear path that makes 100% sense, you’ll find developers who really want to be CEOs, product people who want to do social good, and designers who actually have a passion in robotics.

For all of these, their current jobs are a stepping stone to their long term goals, even if down the road, there’s a point of divergence.

This is where the boring “career development discussion” can actually start shining.

When approached properly, a development discussion process can single-handedly multiply the impact of a person, as it helps them visualize their current role in their personal long term path.
Our transport service operates at 100% conversion because you can’t say no to us.

Embrace the Entrepreneurial Spirits

I’ve had plenty of direct reports with active startup projects on the side. Just little ideas and hobby projects they’ve been working on with their friends during nights and weekends. With a hope that maybe someday that project might turn into something real.

This is usually the kind of thing people try to hide from their bosses, as most bosses immediately go into panic mode of those people spending all their passion on their hobby project.

That’s nonsense.

First off, if you’ve found an entrepreneurial employee, pause for a second to pat yourself on the back. These are the gems you’re lucky to have.

Second, that person’s passion is not a zero sum game. Just because they are putting their skills into something else than the thing you’re paying them to, doesn’t mean their impact on your thing is necessarily impaired.

When you remove the stigma of wanting something beyond what the current company can give them, you make it ok to bring that passion to work and make it elevate their overall output.


Be all ears.

I like to make sure of a few things when running development discussions. I do them bi-annually as that cadence keeps them infrequent enough to always have new things to discuss when people have their long term goals evolve, but they are near enough to keep a good pace of check-ins that go deeper than weekly 1-on-1s can.

1. Book a minimum of 90 minutes and keep them sacred

Don’t rush career development discussions. Make sure you’ve got 90, preferably 120 minutes booked for each member of your team.

Make absolutely 100% sure nobody books over them or that you don’t have any distractions during the talk. This is the most important time you’re spending with that employee in a 6 month period!

Only get distracted if the building is on fire.

2. Make sure they feel comfortable

It’s your job to keep the conversation casual and approachable. Make time to talk about personal stuff, things not pertaining to work, whatever that sets the tone to be casual and relaxed.

You need to be able to establish trust and candor, and that won’t happen if you’re all about the biz.

3. Keep it private

Both in terms of where you meet, and how you approach the conversation, make sure you treat it with the utmost privacy. You are talking about people’s hopes and dreams here, and their current role’s compatibility (or incompatibility) with them. That’s ridiculously private stuff!

If you expect them to be candid with you, make sure you reciprocate with absolute trust and privacy.

Don’t have the meeting in a public space, like a coffee shop — or worse yet, some open area at work. Get a meeting room that doesn’t have glass walls or shoddy soundproofing.

And whatever you do, don’t blab about what you’ve discussed with anyone else, unless with explicit consent from the person themselves.

4. Make them prepare

Have the person do some homework that forces them to reflect on their past 6 months and their current 10 year plan. For most people, being able to discuss these topics requires a lot of self-reflection at first, so try to make them flex their minds by writing out a few things on how their long term plans have evolved and how well they’ve been able to execute on their path.

5. Don’t forget to start by reviewing the past

If you’re with an employee you’ve already gone around the block a few times with, you should have some existing documentation on past sessions. Make sure you start by reviewing where you started out 6 months ago.

Most of the time you’ll both be quite surprised by what you find. Even though in the day-to-day grind things feel like they evolve glacially slow, when you look back at that innocent, naive, and young person 6 months ago, you’ll almost always find that more change has happened than either of you think.

6. Make it mutual

When you review the past, don’t forget to review both sides. A healthy development discussion is not a one-directional review session reminiscent of a trip to the headmaster’s office.

A healthy development discussion looks at the commitments of the employee, the manager and the whole organization towards the mutual journey of growth and impact these parties have agreed upon.

Did the employee follow-up on goals set? Did the manager support the employee’s growth with relevant responsibilities? Did the organization provide opportunities to improve the employee’s skills?

Any party’s falling short of their commitment should be called out and acted upon.

7. Document

While you should be making sure the focus of the session is conversation between two human beings, it’s highly important that the key points discussed and especially the goals set are documented and the documentation mutually acknowledged to make sure both parties understood the conversation the same way.

This is the only way to provide continuous development as the value of the following sessions is multiplied when they can be started with a look back on the previous session from 6 months in the past.

Here’s a nice little template you can steal for your own use:

8. Set goals

As with any plan, most decisions should be at least somehow quantifiable.

The person wants to become a better public speaker? Set a goal for the manager to help with at least three local meet-up speaking gig opportunities in the next 6 months and a goal for the employee to deliver presentations to each opportunity presented.

The person wants to get better at analytics? Set a goal for the manager to provide at least one new responsibility pushing towards that skill set and a goal for the employee to read at least one book on the topic.

A few other tips I’d take into consideration:

  • Don’t make these conversations about money or title. Not to avoid the topic, but make sure your team understands that there is a time and place for salary and promotion conversations, but this is not it. Also make sure to stay true to that promise and manage salary & title expectations properly.
  • Try to avoid framing the conversation as a “performance review”. This conversation should be all about behaviors, not outcomes. Especially related to personal growth.
  • Make sure this isn’t your ONLY personal time with your team every 6 months. There has to be 363 other days in the year where they feel good about talking to you about their careers too. These are just extra-super-special reserved time.
  • Get some feedback from others. You don’t need to make it a huge formal process. Just solicit some overall feedback on how people who work with your direct reports have perceived them recently.
Mutually beneficial relationships beget a lot of high fives! 🙏


I’ve managed a number of different types of people in my career. Everything from completely drama-free stable performers to full-on volatile all-over-the-place fireballs.

Anyone who’d tell you the former are what you want and the latter are the kinds you want to avoid knows nothing.

While the even keel ones are great to keep your sanity and for maintaining a stable course, having some of those fireballs is essential, as long as you can harness their energy.

I once had a designer on my team that I struggled with for a long time. I even wanted to fire them on several occasions as they constantly acted up and made my life, and the lives of all those working with them miserable.

I tried old school methods of “get in line or you’re out” to force them to conform, but I was getting nowhere.

Once I finally sat down with them to properly plot out where they were going long term, I started getting to the bottom of the issue: the person was just bored in their current role and misaligned on their long term dream of working designing advanced hardware (we were just a middle-of-the-road web software shop).

This person was nowhere near ready to take the leap to where they wanted to go as they were still quite junior, but we mutually acknowledged there is a clear divergence point in the future between this company and that person’s journey. After that, the conflict disappeared: the person’s current job suddenly made sense again. It wasn’t traversing in the wrong direction, it was momentum in the correct general direction.

That relationship was never anywhere near as problematic since then.

This is why mapping out and committing to your team’s journeys is so important. If they are just mailing it in for a deposit of 💰 every couple of weeks, you’ll never get the passionate ones, nor make the most out of your time with them.

So stop worrying about lifelong employee retention and start making sure you’re making the time count.

Aligning with the goals of people will get you on a fast track to that coveted prize: motivation.

I’ve been on both the receiving and providing end of really amazing processes like this a few times in my career and both jobs ended up being transformative in my career.

My years at Futurice taught me what a differentiator great management can be and how HR can be a massive multiplier in how a company operates. Their obsession on awesome development discussions made a permanent change in my approach to managing humans. Having a company truly commit to your personal growth — and give you tools as a new manager to help others feel the same — really helped me realize the potential.

At Greatist, I was among the first wave of experimenting with Tours of Duty, transforming how a small company can approach career development in an environment of constant change and volatility. Having that back-bone of mutual commitment to growth and impact was a huge differentiator in bringing the team together.

For more details on all the things I’ve learned about leadership, please read my previous article on focusing on humans overall:

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