Effective Delegation

I’ve been a manager for some years now and have made my fair share and more of delegation mistakes. I wanted to put some thoughts down around the concept and practice of delegation to serve as a guide to new(er) managers.

What is delegation and why we do it?

As an individual contributor (IC), you get work done on your own. You were very good at it which is why you got promoted to being a manager. As you’ve noticed, the job of a manager is two fold. One is to grow the capabilities and skills of your team. The other is about how you get lots of quality work done effectively through the people you manage. When you delegate a task or project — you are tapping into someone else to lead it and the end result should be — great work, done on time and both manager and report feeling great.

An effective manager is able to retain control over the quality and timeliness of the work, while empowering the team to do great work.

How to delegate effectively?

Delegation has been ineffective if the work is not great, not on-time, and both manager and report feel dissatisfied about it. There’s many reasons why we could end up in this state — and if you find yourself at risk for these symptoms, we suggest you follow the box, check-in and close model. The model scales across the spectrum from junior to senior reports. Let’s walk through the model.

The box — ‘I’m going to tell you what I want’

I like to think of any delegation as having some boundaries. The boundaries of what the output would look like, the boundaries of time and who’s involved and the quality etc. There are boundaries. Boundaries represent expectations. Boundaries when put together create a box.

It’s the manager’s job to define the box.

The box is all about the ‘What’. It should not get into the ‘How’ — you want your reports to be empowered to figure out the ‘How’. It tries to define in as much (but not too much) detail what output/outcomes the manager desires. The box should be much more clearly defined for more junior people, they probably have never built what you want them to do before and so details matter. Before anyone runs off to get work done, there should be a clear — preferably written — understanding of the box. For more cloudy problem spaces, start with a less clearly defined box, but know that you will revisit the box itself to add more structure to it. Make sure you ask your report “Do you understand my view of the box?”. Then say “Any time you think the assumptions we’ve made about this box do not hold, come talk to me. Maybe we need to revisit the box”. As a manager, we should be open to revisiting the task being delegated — as and when things change. The box model is also a great tool if your own manager isn’t great at defining things for you.

The work landscape is strewn with the bodies of talented but frustrated product managers who fell down the gap of missed expectations. Fall enough times and you realize it’s about defining the box early and revisiting it as needed.

The check-in — ‘how is it going’

The next thing that makes for great delegation is the process by which you check-in and steer things. Done well, you get to enjoy a task being done exactly the way you want it, and the person doing it feels they are doing their life’s best work. Done poorly, you’ll enter the domain of the ‘micro-manager’ or the ‘over-delegator’.

With the box well established, the role of the manager is to set up the cadence for check-ins. And drive the conversation in each check-in. For someone I’ve never worked with, I make sure I check-in early and often in the beginning.

The check-in conversation is really about these key questions. How are we doing? Why do you feel that way? How are we tracking towards the goals and what happens next?

You listen to the answers and you give small but important course corrections as input which should leave your report feeling like — “good check-in, those inputs improved my chance of success and I learnt something”. Your input should not feel like — “my manager does not trust me and keeps giving me advice”. It helps to sometimes start the first few check-in meetings with “I’m really excited that you are cranking away on this, I want to get caught up and see if I can improve your approach”. It’s their approach. Its their thing. You need to let them do their thing.

Poorly conducted or infrequent check-ins will basically make you feel like a manager that has no control. You’ve actually failed both your report and yourself. The chances of a bad ending are high unless the report is very good at managing up and proactively getting your feedback.

Weekly check-ins are the norm. Check-ins 2x a week in a light format are quite common. Daily check-ins are a form of escalated focus and are done when things are moving very quickly or when the report needs a lot of help. There is no rule, just make sure you are getting the time to properly ask and answer those 3 questions.

The close and feedback — ‘this task is over, let’s learn from how it went’

We work in complex organizations and face complex problems, and so, the journey from the start to the end will have its bumps. The key is to get to the end with the best possible quality, done as quickly as possible with both report and manager feeling great about it. If you’ve done the box and check-ins, I think you usually end the journey in a state where you both feel like you did your best given the circumstances. But it’s really important at this moment to see if you could step back and revisit the journey.

As you talk through that journey, you’re helping each other learn to do the same thing better. Or you’ll be finding patterns that teach you to handle a different situation better. It’s about learning.

Usually reports do not grok the fact that their manager is also an imperfect being and is also improving their game to be a better coach and a better leader.

Tough Situations

In the middle of a hot mess

Some tasks are just fraught with risk. In an environment that doesn’t cope well with failure, the manager ends up with a lot of stress. This is because their report could be failing despite their best efforts, and they feel the desperate need to do something about it… typically they jump all in and become a master of micro-management overnight.

Instead, it is important to work hard to create a culture where failure is not penalized, and that we focus mostly on learnings. The way we create this culture is by having you (the manager) upwards-manage very aggressively. You communicate early that you’ve got a ‘hot potato’ that your team is trying their best to grapple with and make sure they get timely updates. You ensure that your management team is fully aware this task was fraught with risk to begin with.

The key is that you manage that pressure between senior management and yourself and not pass on that extra stress to the report.

You let them do their most focused and creative work — so that the hard problem gets the most focus from them. All the internal strife and challenges around expectation setting are handled by the manager. In the end, should the project still not yield the necessary business outcome, the real success should be in the learnings that it did yield. Highlight these. Move on to the next one.

Cement your relationship with management as someone who can take on the tough tasks, without burning out his team or themselves. Every company needs such managers.

Poor Trajectory

Your check-ins are proving what you were suspecting all along, that the task is going to get the better of the individual report that is trying to tackle it. Don’t hide your feelings. Tell your report that you can clearly see a problem and that you are here to help. Increase the frequency of the checkins. Also start to get to the bottom of why a seemingly tractable issue is getting hard to tackle. Usual suspects are around poor process, poor assumptions or skills themselves. Identify the gap and get prescriptive in how you want the gap fixed. If another team is the cause of the issue, get involved directly to broker a better relationship or outcome with that team. But either way, get very crisp about why your report has a poor trajectory on the project.

Your gut is going to throw the red flag much earlier and you’ll want to fight the instinct to “give your report space” — never hurts to really dig in a little more in one of the check-ins, to validate your gut.

If you see a pattern here, where the report themselves is either unable to take the feedback and resolve the issue or lacks skills that are foundational to the issue, it is time to take some action. Suspending the task entirely is an option, till you can make sure you have the right person to lead it. Swapping who leads that task is an option, though much harder given competing priorities.

Finally, if it is business critical, this may be the right time to roll back your sleeves and dive right in — make it amply clear to the report that we are in this mode because the task is too difficult for them to do on their own, that you are now leading and they should watch and learn.

Being in this situation with the same report multiple times signals a mismatch in their skill-set/abilities to the problem space you are in, and you should consider moving to performance management as the next logical step.