How to have valuable career growth conversations

by David Morgantini

Introduction

This conversation is intended to help a manager or mentor work with someone to help them identify opportunities for growth and set the growth objectives for the future. It also is intended to help a manager identify potential issues that could be addressed to ensure the individual is able to execute at their best. The final goal is to identify organizational issues that you and your colleagues can address. The best way to do this is to ensure that the growth conversation process is joined up and key challenges for multiple individuals are collected so any patterns can be identified and addressed.

This document will go through a set of questions and the reasoning for the questions. The discussion itself is intended to be done in its entirety though you should use your discretion when conducting the interview to ensure that you’re getting the value you need from it.

Questions

Question 1: How are you doing? How is work?

This is a general-purpose question meant to have the individual open up about their current situation. There shouldn’t be very many surprises here depending on how you’ve done your 1:1s but you may find yourself surprised if you’ve not allowed a lot of leeway in 1:1 topics. You’ll want to spend some time practicing active listening and asking clarifying questions to ensure you understand any pain points that might arise.

Question 2: How has the last six months gone for you?

You may change this question or possibly skip it depending on how deep the previous question went and when/if you’ve done this conversation before. The intention is very similar, you’re looking to get a deep understanding of their personal/professional well-being in order to identify issues that they are facing.

Question 3: Can you list 3 achievements that you are most proud of from the past 6 months to a year?

Again, the timing will depend on when you last talked to them. What we are looking for here is a sense of a) is the individual doing things that give them pride b) what patterns exist. In order to be truly happy at work, we need to be achieving things that we are proud of. If the individual struggles to list three this is a clear indication that they may not be fulfilled in their role and might be something to dig into in the future. We’d like to see patterns in their achievements because it can help to inform further career conversations. For example, if later on in the conversation the career goals don’t match with the previous achievements it might be worth discussing this with the individual.

Question 4: Describe your current role?

With this question, you’re looking to get an understanding of how the individual perceives their current role. The goal is to give them a baseline to compare to when considering what the role might look like in the future. If you’ve had this conversation in the past it’s also an opportunity to retrospectively assess how they have done against their stated goals. A clear failure to progress in the goals set might be a good opportunity to reset expectations and try to understand what stood between them and these goals.

Question 5: What do you want your role to look like in 6 months?

We pick 6 months here because 6 months is within the easily foreseeable future. There are still opportunities to make changes in their trajectory but in general, their current team might be set and there is hopefully some sort of plan for the work they will likely be asked to work on. Depending on the seniority of the individual I will rarely editorialize on this. Sometimes, you might give guidance to someone who is struggling and help them summarize their targets. I’ll often make sure that I’ve communicated that I’d like them to do greenfield thinking. Often people will tell you what their role will be if they stay on the same trajectory. What you’re looking for is the ideal world. This will help you understand if the role you had in mind for them will be the one that they are happy to fill.

Question 6: What do you want your role to look like in 2 years?

In contrast to 6 months, 2 years is far enough away that almost anything can happen. I normally caveat this with “if you’re still with the company” in order to help them contextualize their response into what they could do at the company. Again, you’re looking for an ideal world but it needs to be tempered with reality. Most people need guidance here and that tends to vary depending on the experience level of the individual. For more junior engineers I will tend to steer them towards technical excellence as that’s the underpinning of any technical career. For more senior engineers I will explain 4 different career paths (Technical specialist, Architect/Consultant, Product/Strategy (CTO), People Management) and then help them decide how far along any of them they might want to go in the next two years. At this point, it’s also important to make sure that their goals connect back to their achievements in order to allow for more achievements over the next 6 months/2 years.

Question 7: If you were to leave, what’s the #1 reason?

The goal of this question is to understand how close the individual is to leave the organization. One of the red flags you’re looking for is, how easy is it for them to answer the question. If they can list of 3-4 reasons without much thought you almost certainly have a flight risk on your hands. If they answer something along the lines of ‘if another job comes along that offers this’ or ‘if I have an opportunity to…’ then you’re probably also looking at a flight risk but at a lower probability in the short term. Both of these situations are important to address quickly directly with the individual. On the other hand, they may answer something along the lines of ‘if this changes’ or ‘if I can’t do this’ - these are indicators of a low flight risk but still worthwhile to be aware of. Sometimes it’s worth digging deeper into these to ensure that you understand what they are truly thinking about. Other times it’s enough to ask them to let you know if they start to feel like it is in the process of changing.

Question 8: If you had an infinite amount of money & <CTO/Director/High-level technical person>’s job, what would you change?

The goal for this question is again to understand flight risk but also to get a read on the challenges that people are facing. The reason for the infinite amount of money is to remove constraints from the individual and allow them to be creative. Sometimes you might prompt them with some of the frustrations you unearthed earlier in the conversation. The answers to this often don’t require an infinite amount of money and are good ideas you should act on. If you hear it from more than one person it’s a clear indication that it might be worth acting on it.

Question 9: What haven't we talked about that we should have talked about?

This question ensures that anything that the individual feels is important and hasn’t had a chance to voice has an opportunity to be heard. This will often revolve around pay/promotions and you’ll want to be prepared to discuss these if appropriate.

What’s next?

Once the individual has had a chance to answer all the questions you have a few responsibilities.

1) Ensure that the issues raised are actioned or at least discussed further. The value of this conversation dramatically decreases if you do not action or further discuss the issues raised.

2) Work with your colleagues to collate any feedback and identify trends. This will allow you to work systematically to address challenges that might be bigger than one team or individual.

3) Share with them a copy of the notes you’ve taken (and make sure you’ve stored them somewhere you can find them again). These notes will be necessary next time you run this conversation.

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