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Boondockers, Wizard of Ozzing, landing on your feet in your next product leadership role

One Knight in Product newsletter
One Knight in Product newsletter
I’ve been a bit quieter on social media recently, and this newsletter is a little late too, mainly because I started a new job! I’m super excited to be working with the team at Unmind to revolutionise mental health support in the workplace. It’s genuinely a pleasure to be working on problems I care about deeply with an equally passionate team of like-minded people.
Swag!
Swag!
New podcast episodes
Here are some new podcast episodes with a couple of fantastic entrepreneurs!
Firstly, I spoke to Anna Maste. Anna co-founded Boondockers Welcome with her mother, scaled the company through community engagement, and then triumphantly exited. She’s now back with her new company Subscribe Sense and trying to do the same again. Check the episode out here.
Secondly, I spoke to Sophia Höfling, co-founder and Head of Product at Saiga, a new digital personal assistant startup. They’re currently Wizard of Ozzing their way to success, and we also talked about life-centred, ethical product design as well as collaborative product discovery. Check the episode out here.
Book recommendation
You’ve been Inspired, you’ve been Empowered, and now the Silicon Valley Product Group is back with Loved by Martina Lauchengco. This new book steps away from product management principles and focuses on the critically important role of product marketing. I recommend this book to anyone considering their first product marketing hire, or for leaders that are struggling to realise the true value of product marketing within their organisations.
And yes, I’ve already scheduled an interview with Martina to talk about the book. Watch this space!
Landing on your feet in your next role
After spending 19 years working for a big corporate, it feels kind of strange to have started 3 jobs in the last three and a half years. Whatever the pros and cons of working for anyone for a very long time, it’s fair to say that you know the company and the stuff you’re working on pretty well. Then you move on and you instantly feel like the dumbest person in the room!
There are lots of guides out there; books like The First 90 Days and thought leaders like Gibson Biddle have excellent content about their approach to landing on your feet (check out our chat here). But here are a few reflections of my own about how to get off on the right foot when starting that new job. This is written from the point of view of product leadership but I’m sure some of it applies to individual contributors too. I should also point out that this list isn’t exhaustive.
It all begins before it begins
One thing I like to do is start to meet the key stakeholders from the new place before I start at the new place. This might not resonate with everyone, because some people hate the idea of basically doing free work before they’ve started their new gig. And, to be fair, this step is totally optional but I find it a really useful way to get up and running on day one.
Aside from having a general chit chat and bonding, I like to ask a couple of key questions to help understand what’s going on in their world.
  • What’s the most important thing on your mind right now?
  • How can I best help you when I come in?
Whether you can actually fix these things is on you, but knowledge is power!
Don’t be a bull in a china shop
If you’re like me you’ll have opinions about a lot of stuff. Either product management specifically, general organisational design principles or whatnot. It’s absolutely fine to have these, and they’re presumably some percentage of the reason you were brought into the role in the first place.
But companies - even small, newish startups - are complicated systems. There’s an official organisational structure (who reports to who), and there’s the shadow organisational structure (the relationships between people that practically speaking help stuff get done). There is technical, product & operational debt in any company. There will be things in flight that may not make sense to you when you first look at them. All of this is normal and you may well be expected to fix some of it, but going in all guns blazing and trying to change everything all at once is not likely to make you any friends and may scupper any chance of building the coalition you need to affect the necessary change.
It reminds me somewhat of the story of Lou Gerstner, the turnaround CEO at IBM (author of “Who Says Elephants Can’t Dance”), who resisted the temptation to make big sweeping statements and spent time understanding the organisation before making the moves that mattered.
Meet your team & find out what makes them tick
Teams are made up of people, and people are complicated beings with hopes, desires, dreams and opinions. Depending on where the company is at, they might be motivated or demotivated. As a team leader, you’re there to help the team succeed, and the best way to start is to listen to what they have to say. This means both the people that report to you as well as your own boss. Find out what makes them tick, how they like to communicate and what’s on their mind. Find out if anything’s on fire. Try asking them those two questions.
  • What’s the most important thing on your mind right now?
  • How can I best help you when I come in?
And yeah, set up your weekly 1:1s and try to never miss them.
But don’t stop at your team … get your face out and about
There are some people in the organisation who you’ll naturally end up working with more than others, and you’ll naturally fall into a rhythm with these people. But everyone has a role to play in the success of the company, and the success of your product, so make sure to put some decent face time in around the business. Speaking to the heads of all the different functions is table stakes, and the same goes for the company leadership too. But don’t stop there… there are invaluable connections to be made throughout the organisation and it’s your job to make that happen. I like to ask those same two questions just to orient myself.
  • What’s the most important thing on your mind right now?
  • How can I best help you when I come in?
Depending on the size of the company it might take a bit of time to get to talk to everyone, but the more of these relationships you foster the better.
Don’t be a shrinking violet
So yeah, about that bull in a china shop thing. You absolutely don’t want to do that, but you can’t just sit and listen and nod in meetings. You’ve been brought into the company to make a difference. You are going to be doing a lot of listening, a lot of analysis, and a lot of finding your feet. But you can and should speak up on matters that you have expertise in. Be prepared to eat humble pie if you’ve said something that is kind of dumb in the context of the company or the product, but you have skills and expertise to bring to bear on hard problems and you absolutely shouldn’t shy away from that.
Using your newness to help the team
There’s always a honeymoon period when you start a new job. People are trying to work you out, you’re trying to work them out. You don’t have a 100% grasp on the product or the team. You don’t know the history. You’re relying on first principles thinking for the most part. This is all to be expected but on the bright side, you’re not responsible for anything that’s not working well (I think you get about 3-6 months’ grace on that). You get to ask the questions & challenge the things. That’s to say, take this opportunity to challenge things, ask dumb questions or speak up for your team around issues that they are struggling to be heard on.
Start to grok the company & the product
Ideally, there’ll be a bunch of documentation about past and current initiatives, videos of old Show & Tells, strategy documents and the like. You need to consume as much of this as possible in the gaps between all those meetings that are appearing in your diary. Get to grips with the company’s mission, vision, strategy and principles. Try to work out if your team lives & breathes these, or if there are any disconnects. Get onboarded onto your product as if you were a new user (take lots of notes about the onboarding flow) and start looking at user analytics. Get on some customer calls early, even just as a fly on the wall, and start to understand what difference you’re making to people (and any common frustrations).
If you have a product vision & strategy already, that’s brilliant. If not, make one. It doesn’t have to be perfect … I love Gibson Biddle’s take on the S.W.A.G (stupid, wild-ass guess). You can present this to the team, get chastened at your flawed assumptions and adapt it. This is all good stuff and the process of synthesising the insights you’re getting is just as beneficial as the output.
That's all folks
TL;DR Starting a new job is tough but it’s fun and energising. There are things you can do to make it easier. Also, don’t aim for perfection - this is a process and us agile types should adapt and change to the circumstances in front of us. Good luck!
Thanks for reading! I hope it was helpful. Please share with all your product-aligned friends and feel free to shoot me an email if there’s anything you’d like me to waffle on about in a future issue.
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