Meeting deadlines while mentoring

I’ve been asked to mentor/coach junior PMs in the team and although I understand that I need to be patient and should not be prescriptive. I am pumped for the opportunity and truly believe that I’m giving forward to all the wonderful people that have mentored/mentoring me. But I have a situation.
I have a fast approaching deadline (< a week), where I am putting together a major proposal for my product. The audience is CTO and the CPO. So, the deadline is super critical for my product and my career. What are the best ways to engage my mentee in ways they feel valued, but not overwhelmed. Where I come across as supportive but not prescriptive?


My suggestion is to create one or many working sessions and bring them into the room. Discuss how you’re thinking about building the proposal and what their thoughts are on it. Or have them review your work and understand if it’s clear. Basically bring them into the room with you. They’ll enjoy getting to work on a product proposal and will also learn from how you’re thinking about the product. You may also be able to delegate some tasks to them as they’ll be in the loop on the proposal.


It sounds like this is your project and you are the directly responsible individual. If so, you should go ahead and drive the project and do what you need to do to impress the CTO and CPO. But like @Donovan said you can definitely bring your mentee along for the ride so they can see how things get done. You can also involve them in working sessions but first priority should be to make sure you’re doing your best work. Having them help out with something that misses the deadline or expectations is less valuable than seeing what great looks like.

Also for mentoring early career PMs, in my experience coaches and managers are often not prescriptive enough in many areas. I’m happy to chat more if you want to DM me. I’ve managed 7 early career PMs in the past 5 years. Happy to talk about my experience and I’m available for hire as a coach if you want to do something more recurring or in depth


Besides the wonderful advise @Donovan and @Karan have give in focusing on the project because it’s the day job. Here is some perspective to the balancing act of prescriptive vs supportive having been on both sides of the table. As a junior at some point in my career, I appreciated the prescriptive more than the support. Why? I am fresh/newbie/empty book, I want to learn everything you are doing and why are you doing that? Why did you put that slide before that one? Why are you choosing those numbers before those and why this narrative? Why did you not have that conversation in person or not put up fight when the other person was clearly wrong about the strategy conversation?
Supportive is expected as part of the social contract between a mentee and mentor - it’s not an option or something optional. However - as a mentee I want to learn everything from you and you can’t teach without being perspective but be perspective with an aim to illuminate not dictate. THAT is the key difference between a so and so mentor and a great mentor. Once the mentee has a solid footing, boom, wait till they start asking amazing questions that will even teach you a few things; been there and it feels great to learn something new.


Some good advice on this thread.
@Karan would you be open to sharing an example of how managers are not perceptive enough? I find your answers very thoughtful and would love to know/read (if you have written) on how you approach mentorship to early career PMs.


Ok this should probably be a blog post, but here’s a top of mind, unedited version.I’ve seen three trends for not being prescriptive enough.

  1. Not remembering what it is like to be a beginner. Especially if you’re rather experience, it can be hard to remember what it is like to not know what a requirements doc should look like. Or not be familiar with the concept of scope creep. Or not know how to run a meeting. Many of these hurdles become invisible and the skills needed to overcome them are now intuitive.

  2. For early career product managers you’ll need to break down your intuition on how to solve small problems into smaller steps and decisions. And while a lot of things “just depend” you may need to give oversimplified rules of thumb until they can gain their own intuition.

  3. Not being close enough to the work to be able to give detailed advice on how to proceed. This is totally fine for senior product managers. They have the ability to work on ambiguous problems autonomously, but dangerous for early career product managers. Senior Product Managers are expected to take poorly defined problems, give them structure and lead the team towards a clear, tightly focused solution or experiment.

  4. Early career PMs need to be given a clearly scoped problem and often they need help structuring potential solutions and keeping them focused (for example preventing scope creep).

  5. A natural tendency as a manager to try and not micromanage. If you compare with working with engineering, design or other cross-functional partners you may have lots of instincts that keep you from getting into the “how things should get done” because it falls into another functions domain. For example not telling a designer how to do wireframes.

  6. However, when you are coaching within product management you are the expert in the skills they need to be practicing. Also what would be considered micromanaging for a more experienced PM will be necessary for someone who is brand new. The skill lies in being able to give very detailed guidance but also giving guidance on where they can or may need to diverge from guidance. Pointing out places that have more uncertainty and when they should be more alert can be very helpful.

  7. You should also give guidance on when and how they should ask for help.

So what’s a good way to approach this? I’ll use the metaphor of teaching someone to drive a car.So you are teaching someone to drive and they are approaching a large curve in the road. As an experienced driver, you don’t think about the curve as an active decision. You may even be daydreaming and not realize there is a curve. You can subconsciously adjust your speed and steering. Beginners don’t know how to do this. And you need to give break down your subconscious decision making into discrete steps for them.For me there’s two things to pay attention to.

  1. The steps it takes to solve the problem (driving around a curve)

  2. The foresight to know if something is going wrong.

  3. You know how your heart rate speeds up if you take a turn too quickly? Frighteningly, beginners don’t have that instinct. They happy speed into a turn. Often times they realize they are in trouble too late when things are irrecoverable.


So for beginners you’ll need to break this down into steps. You’ll need to tell them:

  1. When should they start slowing down. Don’t tell them it depends on the current speed, desired speed, shape of the curve, and model of car you are drive. Tell them that for this curve they should start to slow down about 200 meters before the curve. Or if they aren’t able to easily to calculate how far 200 meters is, you may need to say “You’ll need to start slowing down soon… In 3, 2, 1, now”
  2. You’ll need to tell them what the desired speed is for this curve. Yes this again depends and there’s a range of speeds that are perfectly fine. But don’t tell them that. Tell them they should slow down to 40 kmph. You may need to remind them to maintain this speed during the curve and not continue to slow down.
  3. You may need to give guidance on how much steering is required. You may need to tell them when to start to turn the steering wheel. You may need to tell them to turn harder or more gently depending on how they are doing. If it is an uneven or asymmetrical curve they may need to adjust during the curve. You may need to tell them when to straighten the wheel out.
  4. You’ll need to tell them when to accelerate again. This is somewhere between the apex of the curve and the end of the curve, but don’t tell them that. You’ll probably want to tell them in real time when they can start speeding up.
  5. You may need to prepare them for what is after the turn. If it is a winding road, you may need to prepare them for the next curve before they finish with the first curve.
  6. And finally since they don’t have intuition for when things are about to go wrong, you’ll be relying on your instincts. You’ll need to be the one to call out real time adjustments like, “Slow down more” or “Turn more gently, you’re about to drift into the next lane”

@Karan, a lot of this resonates. Through my career I have more often erred on giving less direction than more because I myself never appreciated being micro managed.
Thanks for sharing. That example is great.


@Karan that is some great advice. I truly appreciate it. For someone who also happened to learn things the hard way ( without someone prescribing what to do when and how), as much as I would have loved some prescriptive advice, I am also thankful that I got to figure things on my own. I believe that I am a stronger PM coz I know how not to do things in a 1000 ways for a given situation, but how exactly to do things to get through.
I’m sure my mentors recognized that and that’s why let me figure things out sometimes.
So, how do you know when to let them figure things on their own? How much of a fall, is a…. good fall, so they can rise higher?


Thanks! @Mario.

@Jesus I haven’t had an issue of PMs not learning how to figure things out on their own. There are two things that I think have prevented it:

  1. I think of my job to help by giving tangible guidance. I’m not driving the car or doing the work. (In some cases I’m doing the work but the goal is to transition the work to them under a specific timeline). I also like to caveat a lot of my guidance as, “I’ve thought about this problem for about 30 minutes. You’re going to spend a week on it before our next 1:1. It’s likely that by spending a lot more time on this, you’ll have learnings or realizations I haven’t had. Most of the time you should do what you think is right and just keep me updated. You can also always reach out and we can do a quick huddle to discuss”
  2. My calendar. I am busy enough where I can’t spend enough time to give them step by step guidance on everything. I’m usually doing a mixture of:
    A. Preparing/scoping/clarifying work for them to do.
    B. Giving guidance on work I’ve asked them to own.
    C. My own work. And honestly,

I’m spending the majority of my time on C.


Thank you @Karan, makes so much sense,

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What @Karan so eloquently described is similar to a framework called “Situational Leadership”, The basic idea is that people are not “good”/“bad” or “new” /“experienced”, but that for each task, they may be somewhere along a journey of low experience to high experience. And that their confidence also swings drastically along the journey. So there are times when a task might be really new to your mentee, and they’ll need directive coaching, while another task they might need more cheerleading or Socratic questioning. The most important thing I’ve found is to make sure that I adjust my coaching style to the task, and not treat the person as a monolithic “experienced” or “inexperienced”,

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Oh I love this! @Michael, who do I cite when I use it as a reference?

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Situational Leadership Theory is a model created by Paul Hersey and Ken Blanchard. Been around since the 1960s.