How to Help Your Team Members With Career Grow 🪴

Because they deserve someone on their side advocating and sponsoring them along the way

Apr 17

Happy Sunday, friends 🐣

This week, I’m writing from Breckenridge, Colorado. Our family is spending some quality vacation time together mostly swimming, “hiking”, and eating great food. Plus, hunting for a troll 🧌. I’ll let you know if we’re successful in our expeditions next week!

Today, we’re talking about career growth inspired by some posts from Erik Torenberg - The Career Education Paradox and See Your Career as a Product. Specifically, we drill down on a few reasons why I feel like career growth is such a squishy term and some tactical steps for managers and leaders based on my experience.

This is my longest post yet (2,000 words) - buckle in! I hope it’s valuable. Let me know either way!

Cheers,

Jeremey

Thanks for being a part of this newsletter. Every Sunday evening, I send a note about solving problems and helping customers. Please say hi (reply here or at jeremeylduvall@gmail.com). I’d love to hear from you.

We can all agree growth opportunities are good!

One of the questions I’ve been asking candidates for the Support Specialist role at Ness is what specifically they’re looking for in their next role. Most have described “growth” in some form or another.

This makes total sense! (And, I’m all for it.)

Regardless of whether your desired trajectory is gradual or steep (more on that in a sec), there’s an inherent satisfaction in growing existing skills and developing new ones over time (Dan Pink’s “mastery” right?).

Looking at the other side of the equation, I’d generalize that any good leader also wants to help their team members grow. Doing so helps retain talent and improve performance ultimately leading to better outcomes for the whole organization. Most companies recognize this! Continuing education budgets are increasingly common particularly within the tech sector.

So, both parties - team member and manager - recognize that growth is important. Why then does it prove so tricky to execute on?

I’ll posit two reasons:

It’s difficult to get really tactical on what career growth really looks like in the day-to-day. What courses should I take? What skills do I need?
There’s little guidance on how to approach growth with your directs ←💡 I think we have a great framework on this at Ness that we’ll be sharing in the future!

Let’s dive into both.

A steep vs. gradual disclaimer

At Zapier, I was introduced to the terms “gradual” and “steep” regarding career growth. It’s worth calling this out for two reasons.

First, someone’s growth expectations can change over time for a variety of reasons. Those on a “steep” path are eager to make big jumps and tackle new opportunities. “Gradual” folks are more content with incremental steps. Neither is right or wrong. Just different.

Second, left unchecked, our natural assumption is that the people we lead want to be managed the same way we want to be managed. Through this lens, if we’re in a “steep” phase, we expect everyone to be in a steep phase and vice versa. Spoken out loud, this is obviously untrue.

Should out to @susanavlopes for this tweet I came across:

Susana Videira Lopes @susanavlopes

Key lesson 1: Not everyone needs or wants to be managed the way you like to be managed. Being a good manager is about adapting your methods to meet the person where they are, taking into account their personality and career story. People bring a lot of baggage with them to work.

Now, let’s dive into career growth specifically regardless of the trajectory.

So, why is career growth so squishy?

I’ve certainly sat down with individuals on my team intent on having a “career growth” conversation only to make little progress over the next 30 minutes.

Why might this be?

Problem 1: The job you want seems out of reach.

Imagine you’ve invested 10 years working in Customer Support, but you want to venture into Engineering. Yet, every Software Developer role you see requires 3-5 years of experience minimum.

This presents quite the conundrum! How do you navigate the transition without wasting the 10 years of career capital you’ve built?

(My answer: You build junior roles and set career pathways at your organization. You offer people on-the-job side projects. You help people translate their past experience. More below!)

Problem 2: The job you want hasn’t been invented yet.

The world is moving very quickly. New roles pop up each day. “Growth hacker” wasn’t a term two decades ago. Heck, “customer success” feels ubiquitous now, but it wasn’t formerly introduced until 2013.

Perhaps you’re accumulating a set of seemingly unrelated skills or have your eyes on a role that isn’t yet well-defined. This makes it hard to build a game plan for your career.

(If this is you, I’d suggest reading See Your Career as a Product, Scott Adams’ career advice, and So Good They Can’t Ignore You.)

Problem 3: The skills needed are constantly changing or unclear.

I love this quote from A More Beautiful Question:

In a time when so much of what we know is subject to revision or obsolescence, the comfortable expert must go back to being a restless learner.

Roles are subject to constant revision. The nuances of a Product Manager role today is different than one 10 years ago and will be different than one 10 years in the future. When you combine that with more nebulous skills like “be a systems thinker”, it’s tough to line up tactical next steps.

(See below for some ways I think scouring job descriptions can help with this!)

Problem 4: “Growth” isn’t easily visible.

Early on in your career, it’s easier to check off items on your career bucket list. Everything is new!

When you’re mid-career and beyond, these opportunities are more rare. How often are you really tasked with managing a large-scale change within your organization? (Hopefully not super often!) It’s also more difficult to tie the courses you’re taking into tactical I-know-how-to-do-this-new-thing takeaways.

(Managers should help with nudging for tactical takeaways and tying “growth” back to tangible outcomes! Again, more below.)

Problem 5: It’s difficult to know exactly how best to acquire a new skill.

Erik hit on this in his recent Substack post with two points:

“Most of the world’s knowledge is trapped inside the heads of key operators. The best and most effective teachers in any given discipline are actively building, and don’t have time to teach.”
“Learning content that is even just 2 years old can quickly become useless, as the fast pace of innovation means that previously useful skills can quickly lose their value.“

(Big shout out to maintaining an internal list of recommended courses within your org and a high five to anyone maintaining an external list for roles and industries!)

Let’s get tactical

Here are some tactics to sidestep the problem above and make career growth very action-oriented for your team.

1. Set up with regular conversations.

Establish a regular cadence for talking about career growth. Personally, I’ve found that a quick touchbase once per month and a deeper dive every quarter works well.

In the first conversation, it’s important to set some ground rules on responsibilities.

As a manager, you’re responsible for helping to shape the plan, sharing opportunities, sponsoring them across the org, and generally providing guidance and accountability.
As the individual contributor, they’re responsible for setting the course and destination, building the plan, and actually doing the work.

In every conversation, revisit three questions A) are we feeling steep or gradual? B) what’s the next tangible step here? and C) what opportunities should I (your manager) be looking out for to send your way?

2. Get crispy on skills that ladder up to a role.

“I want to eventually be a product manager” is a great first step, but it doesn’t tell them what to do tomorrow to move them closer to the goal.

If the next step is a specific well-defined role or job level, here’s their plan:

Find 10 job listings for this role from various companies they admire. Internal experts in the role area are often a great resource as well! Alternatively, if this is a leveling jump, make a specific list of qualifications for the next level.
Make a giant list of the qualifications across each role they find (or for the next level). Then, group them based on commonalities.
Now, turn those broad commonalities into interview questions. (i.e. “Experience building a product roadmap” becomes “Tell me about a time when you launched a new feature or product? Specifically, how did you manage multiple stakeholders and make tradeoffs?”)
Have them set up a “Brag File”. List out each question and their relevant experience (help your people get creative with tangential experiences!). Set a reminder to update this every month.

If they don’t have a clear set of experiences for a question1, that’s a potential area for growth. You can then target courses and projects to solve for that gap.

If the next step is not a well-defined role:

It’s entirely possible that they don’t have a specific role in mind. That’s totally fine! I’d encourage them to read Build Personal Moats and identify:

A skill or area of their work that really lights them up. Ask questions like, “When you’re feeling really energized at work, what are you working on? If you could spend more time working on a specific part of your job, what would it be?”
A current gap for the team where they excel. Ask questions like, “What’s easy for you that seems tricky to others?”

These are areas where you could help them double down and really develop expertise (plus, level up your team in the process!).

3. Go into action mode.

Completing Steps 1 and 2 should give them a list of skills to further develop specific to where they want to head. Now, help them scope out an action plan. I think of this in three buckets:

Where can you learn? This category defines articles, books, courses, etc that teach specifics about the new skill or area.
Who can translate? Connect with insiders within the role or industry to help translate the coursework into what it’s like in the day-to-day.
How can you demonstrate? What projects could you work on that turn your broad new set of skills into reality?

An example from my days of wanting to be a JavaScript Developer:

I learned by completing multiple online courses about JavaScript and specifically ReactJS.
I translated by setting up weekly 30-minute mentorship sessions with a JavaScript Developer at Automattic so I could ask them questions about projects I was working on or areas I didn’t quite understand.
I demonstrated by making 120+ pull requests to our open source repo on GitHub.

Ultimately, I didn’t become a JavaScript Developer, but I do think I developed a greater appreciation for the learn/translate/demonstrate approach.

4. Sponsor them!

This is a critical responsibility when you’re leading a team. How can you share opportunities, delegate projects, spotlight work, and generally raise people up?

For an answer, I’d direct you to Lara Hogan. I find myself reading her post on the subject often. Sponsorship requires active energy and focus to do well.

5. Make it all visible and real.

I alluded to this briefly in an older article for Doist. My sense is that many well-meaning career growth discussions fail to fully close the loop in three ways.

Career growth isn’t talked about publicly within a company. That means like-minded people pursuing similar opportunities can’t learn from one another. It also means that new team members don’t have a great example to follow.
We don’t revisit the skills gap to make the checkmark. See above about growth not being visible.
Growth isn’t tied back to the company or role. Taking a course is great on its own. Even better is taking a course and then bringing back tangible action items to make your company even better moving forward.

This step can take many forms, but I’d encourage some form of periodic updates, even if it’s just amongst your individual team. Share courses you loved and what you’re working on. Highlight articles you’re reading or ways you’re growing yourself. Implement the ideas you’re learning about within your team - no harm in trying something new.

Phew…

Apparently, I had a lot to say about career growth. Would love your feedback!

An entire post could be written about job qualifications and how they encourage imposter syndrome and discourage applicants that don’t fit 100% of the list. I have strong feelings on this topic, but I think the general exercise of looking at the broad patterns for a role is still helpful. This is the easiest way I’ve found to do it.

Jeremey DuVall’s Newsletter