How Do You Know When It’s Time To Go?

There’s a lot of ground to cover here and after 10+ drafts I’ve figured out that I can’t write about everything and still make this readable, so here’s some context:

• The target audience I’m writing for is people who haven’t changed jobs a lot. Customer Success at Microsoft was my 17th job and I still struggle with the “when is it time to go” but I remember it being way harder when I quit my first job or when I shut down my first start-up so this my way of sharing some of what I’ve learned since then.
• This isn’t about crappy jobs. Jobs where your manager sucks or you get treated unfairly or harassed or discriminated against. If you’re in one of those jobs, a LinkedIn post really shouldn’t be the driver for you to change.
  This is about those jobs that are actually pretty awesome, when you’ve got a good company, with a vision you can get behind and a good manager and good pay for the work that you do and probably even prospects if you keep your nose down and do good work for a couple more years. That’s a good job by pretty much any definition, and that’s the one you really agonize about because in ten or twenty years time you will start asking yourself “what if…”
  Let me help you get to that question quicker!

With that out of the way, three takeaways – the second one is pretty Customer Success specific but the other two should work for everyone:

1. Go where? There’s a lot of nuance to this. ‘Go’ doesn’t have to mean leaving your current company (although it might!), it means finding your next challenge. But this requires you to understand the lay of the land. No one is going to come to you and say “Tim you’re amazing as a CS, come work for me in Sales” or Product or anywhere else in your organization. I mean, maybe they will to you! But I’ve not had that experience. Every one of the 17 jobs has been because I’ve applied for the role. Now it’s possible that this is because I’m not that great at Customer Success but I suspect that it’s because, in a most organizations, that’s not how things, work most of the time.
   • So the key point here is that you, and only you, are responsible for your career. Not your company, not your manager, not your HR person, you. Other people can help, absolutely, I’d encourage you all to be putting regular time in your managers calendar to check in on your career. Get another perspective on where you are on the mastery curve, tell them what you are enjoying and ask them what kind of roles they think you’d be good at. Leverage those resources, but own your own journey.
     • And remember it’s not a tunnel leading to Satya’s role, the best advice I ever got was that your career is a pond and all across the pond there are rocks. At the other side is your goal. Maybe it’s being a CEO, maybe it’s being a technical expert, maybe it’s retiring at 40. And there are many paths to get there, sometimes you’ll jump from one rock to another, and find that this is not the rock for you and you need to go back. Sometimes life happens, you have twins (!) and then you need to look at the rock you are on and decide if, hey, this rock is pretty good for a little while, it’s not my goal, but I can stay here a bit because there are other things in my life that need to take priority right now. But we’ll come back to that later…
2. When you lose your empathy: the secret to great Customer Success is having empathy. Placing yourself in the shoes of your customer and understanding what they want to achieve and how they are trying to achieve it. And that’s really taxing; it’s the reason that a lot of CS people burn out. My working theory is because if you do this right, you see a lot of the problems with your own product or organization and so you have this dichotomy within you, where you have a problem but you are unable to resolve it (because in most orgs, stuff doesn’t move fast and CS doesn’t change how the product works). Over time this builds up until bad things happen. Be aware. Manage this and when you can’t do that anymore… change.
3. When your priorities change: “Thanks for that deep insight Tim, yeah…” but how many of you actually know what your priorities are? Microsoft has a week every year that they call “Trust week”. It’s a chance to reflect on things like ethical decision making and understand a little more about how to support and grow that internal voice that guides you. Two years ago, we had a guy come and talk to us about what the warning signs were that people were going to make unethical decisions. Super interesting talk, I don’t remember his name (if any of the MS people can, please let me know so I can link it !) that I’ve left but one of the things that really struck me was that these people, the ones who faked the Volkswagen emissions tests, the ones who omitted the 737 MCAS info when working with the FAA. These weren’t bad people, these were engineers and pilots who were put in untenable positions, their organizations saying to they “you need to product these results or you’re out of a job”. And with the benefit of hindsight we can act all shocked and “how could they have done that” but in the end, it came down to what was a priority for them, and the priority of keeping their job vs. maybe getting found out, maybe not, at some point in the future… So, the bad news, you will have to make a similar choice at some point in your career, I guarantee it. By virtue of reading this far, it’s clear that you are a high achiever, driven and engaged, and so you’re going to be put in this position at some point, as a result. One of the ways you can build a defence against making the wrong decision is by understanding what you’re going to prioritize. What’s important to you.When I was doing my MBA, a mentor of mine, Ryan Gunesekera, gave me an exercise with a set of cards… 3 categories: Important, Not so Important and Very Important. I had to sort 70 cards with values on them, into those categories. Eventually what I ended up with was a stack ranking of what was important to me. I found this super valuable, because I don’t typically have a problem choosing between a good thing and a bad thing but it’s when I’ve got to choose between two good things (do I work a little longer on this project that’s going to help my customer vs. spending that time with my daughter?) understanding which consistently comes first really helped me. I’ve made it into an online exercise here: http://principlestack.com/ It should take about 20 minutes and I do it every couple of years and it evolves (because you change!) as a reflection of what’s important to you. If you have any questions or want to chat about it after you’ve done it, more than happy to talk… I’ve got plenty of time right now!

Wrapping up, I want to reiterate the theme that I suspect most of you picked up on in maximizing value while at MS section, the thing that’s worked really well for me has been to create value for other people. If you want a quick thumb suck test on whether what you are doing is valuable, reverse the roles; would I be happy with this service/product/treatment? I’ve found that a consistent benchmark both professionally and personally, if you can deliver the level of service that you would expect to be given, you’re gold. You’ll win the trust of the customers you’re working with the the results and accolades will follow.
It’s been a fantastic experience, creating value for our customers, learning and building at Microsoft and working with you. I’ve made life-long friends, done things I’m incredibly proud of, been challenged and grown as a result. Thank you all for contributing to that, don’t be a stranger, and if I can help you, or if you even just want to bounce some ideas off someone, please reach out.

Thank you!

Thank-you and goodnight

Now a quick caveat, I spent 3 years at MS… that’s a little while, but it’s not 20 years and my insights reflect that relatively limited experience, this is what worked for me, maybe you’re the same, maybe this is just an interesting set of datapoints about how other people think about things… either way I hope there’s value here for you:

How can you maximize value while you’re at Microsoft?

1. Build networks: especially when you’re early in career, you’ve got at least another 40 years if you want it, the tech world is small, Switzerland even more so, chances are that you’ll interact professionally with others again. Create value for others by doing good work because this will follow you across your career.
   • A side note: Beware not updating your previous impressions. I did an MBA 10 years ago, if I was to get back in a room with those people now, what preconceptions would I start with? What heirarchy would I expect to ‘naturally’ emerge? The cool kids, the ones who went to McKinsey, the ones who started companies and built empires. Despite knowing these people incredibly well 10 years ago, they’d be almost strangers to me today, in terms of their experience and their abilities. You learn and grow every day, so does everyone else. Update your priors… and leverage this to your advantage. Create value for others and they’ll engage readily in the future.
2. Learn: MS has some amazing opportunities to learn, we all know the MOOC’s, they are exceptional. Do them all. There’s also a lot of mandated learning, don’t let that deter you from investing some of your time into building the skills you want to invest in. Chat with your manager, allocate time every week, build a habit. Microsoft gives you the space to learn, don’t waste that.
   • Try something new. One of my highlights was speaking at the MS technical conference about “what’s not going to change in the next 10 years” with Emma Stephen. Was it a strictly technical talk? Not really? Was it something Dev’s need to think about if they want to deliver a great product, absolutely. Create value for others.
   • Teach others: the one thing that will accelerate your learning the fastest is teaching others. Here again, you are creating value for other people. Learning on it’s own is actually pretty useless, it’s only when that learning is applied, when you do, that you add value to the world but that cool this is that you can 10x that really quickly, by teaching others what you have learned. You’ll understand it better and you’ll establish expertise (remember the bit about impressions above!)
3. Understand the mastery curve: so my ballpark calculation is that it takes between 3 & 5 years to master customer success. There are a couple of dependencies: have you worked in CS before; do you understand how the company works and how your customers work? Some of this is experience based, but you pretty quickly run through the permutations of the problems you’ll need to solve. As you go along this curve, what you spend time on changes. In year 3 you’ll be able to manage your customers in 60% of the time it took you at the start, at year 5… it might be 20%. That’s how good you’ll get. So it’s important that you evolve with the role, it’s important that you shift to teaching, it’s important that you find passion projects that inspire you and do more than just add usage or seats, it’s important that you keep learning and trying new stuff because that will extend how long you can do this role successfully.

Stay tuned for the second part, later this week: How do you know when it’s time to go…