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One-on-One: Better Professional Development Conversations

One of the most rewarding — and coincidentally, the most challenging — aspects of people leadership is creating space for professional development conversations with direct reports.

I’m super tactical naturally, so the things that I gravitate toward are around what people are doing, how they’re doing it, and then making sure why they’re doing it is aligned with our team’s OKRs. 

This is a dangerous road. If you go down it, you will find your team’s engagement dropping, their loyalty to the company ebbing, and ultimately they will leave your team or your company for something else. 

If I’m not careful, I’ll focus 100% of my one-on-one time on these types of short-term day-to-day things and never create space for conversations that equip and empower my team to talk about and figure out what their next growth step is.

This is a dangerous road. If you go down it, you will find your team’s engagement dropping, their loyalty to the company ebbing, and ultimately they will leave your team or your company for something else. 

WordPress and the Great Resignation

Yikes, that’s dramatic but we’re going through a ‘Great Resignation’ period for a reason. We’re just as subject to this in the WordPress ecosystem as everywhere else. 

If we take a step back as people leaders, we know that feedback is an incredibly powerful tool in helping our teams get better. Yet, one of the challenges many people leaders face is not knowing what to give their direct reports feedback on. 

We get stuck in the weeds of specific task feedback or celebrating outcomes. While these are great things to acknowledge, they don’t necessarily provide the depth of insight that would identify the how or why of an approach that could be repeated and refined to the benefit of the team member and the team.

I believe we end up in this situation because we don’t have clarity as people leaders around what success is for each of our direct reports and we haven’t worked with them to define their development roadmap. 

Be clear about what someone would have to be able to do to fill your shoes.

Here are a few ideas and ways you can change that and make professional development conversations less fuzzy and more concrete for you and your direct reports.

Professional Development Isn’t a Performance Review

Professional development and performance reviews are two sides of the same coin with two different outcomes. A performance review is a look at the past and how someone performed a set of specific tasks. You might include some feedback on areas for improvement but it is primarily about the execution of work and is often only something that happens occasionally.

Professional development on the other hand is forward-looking. It’s about aligning with your direct report around their future work aspirations and developing a plan to help them achieve that goal. It’s also something that happens frequently and consistently. 

Yet, they are also linked and when we are proactive in defining a professional development roadmap with our direct reports, we are also creating a foundational performance plan that can be more specific, motivating, and less scary. 

For example, if my goal is to become the editorial manager for content marketing and I’m currently a writer, my performance reviews gain focus on not just what I deliver but how I deliver and what I would need to improve on in order to achieve the professional goal I’m working toward.

When we are meeting consistently and discussing professional development, we are also regularly micro-dosing our direct reports on their performance. This is truly impactful in that regular formal performance reviews will contain fewer (if any) surprises and will likely be much easier for both the people leader and direct report to write.

Start With the End in Mind

As a people leader, any time you are working with people, it helps to have an exit strategy. What I mean by this, is that you should be clear about what someone would have to be able to do to fill your shoes. This is not just at a task level but at a competency level too.

Will they need to be able to develop strategy, facilitate productive meetings, understand tactics and break them down into tasks for the team, communicate cross-functionally, provide feedback to others or manage up, etc.? 

Eventually, you will want to move on to something else or get promoted. The neat thing is that having an exit strategy can give you an early set of core competencies you can be looking to evaluate and elevate in your direct reports. A good people leader, in my opinion, is someone who figures out how to work themselves out of a job. As scary as that sounds, it actually helps you transition from being a task manager to a people leader. 

The added benefit of coaching your direct reports on these things is that it gives you someone to depend on when you want to take a holiday or need to step into a different project for a while. 

Add Professional Development To One-On-Ones

I don’t know if you’ve ever sat through a “professional development” meeting with your manager/people leader before but they can be really painful and awkward. Suppose a manager isn’t equipped with their own roadmap for a direct report. In that case, the most likely scenario is that they ‘empower’ their direct report to own their development and put the responsibility on them to come up with a plan.

I call it the ‘Blank Canvas’ Tactic and to be honest, it’s really hard on both the manager and the team member. Starting from a blank canvas and being asked to create something from nothing with little to no feedback from your manager and little idea of what the possibilities are is extremely difficult and can erode psychological safety.

I think it’s valuable to have a kickoff meeting and an alternative to the ‘Blank Canvas’ Tactic is to come to the meeting with your own plan ready to go. Not only does this communicate how much you value your direct report (because of how much time you’ve invested in their development before you even meet about it), it gives them something to respond to and co-create on. 

However, if the plan is developed but there’s no ongoing accountability or feedback on progress, it can be quickly forgotten and deprioritized. If it’s out of sight, it’s out of mind. 

By integrating check-ins into your regular one-on-ones, you remind yourself and your direct report that you are working toward something greater, which is incredibly motivating.

Be Proactive About Professional Development And Have A Plan To Recognize Results 

Professional development must be a proactive effort by any people leader. Because it is almost always a ‘tomorrow’ outcome it is likely the first thing to be dropped in favor of a ‘today’ outcome. We’ll be guilty of it and so will our teams. Don’t be tempted! 

We communicate so much in what we do and what we choose not to do. Every time we miss professional development because we “ran out of time” in a meeting, we communicate. We have to be the disciplined ones and do what we need to do in order to make sure the future success of our team members is front and center. 

One way to keep it a priority is to attach outcomes to the effort. We do it with our regular work, why wouldn’t we do it with professional development as well? 

If your direct report is successful in their professional development effort, what can you reward them with? Are there milestones along the way that can serve as motivational boosts? 

For example, maybe their goal is to become a C-suite executive. That’s awesome but if you’re not in a position to give them a spot there, what else can you do to reward them? Can you adjust their title, salary band, or responsibilities? Can you send them to a conference or give them a professional award or a public profile on your company blog?

I think that recognizing the effort along the way is just as important and possibly more important than the final destination when it comes to professional development. If your team and your leadership are a really great place to be, chances are your direct reports won’t want to leave anyway. 

Recognizing the individual growth of your team members and encouraging them to go after more will likely result in lower turnover and higher impact.

So what are you waiting for?! Start having better professional development conversations with your team. You can do it, I believe in you!

The Path to Better Professional Development Conversations

  • Create space in your one-on-one framework for professional development conversations. It takes discipline to avoid the tactical but the outcome is better.
  • Decide early on what the core competencies are for a junior, mid and senior level of the role you want to hire or have in your team.
  • Develop an evaluation matrix or 9-grid that you can share with your fellow managers to help you assess individuals and make promotion decisions.

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