This is a very simple question, but one I’ve struggled with at work and home. In the early years of my marriage, I would sometimes (ok often) ask my husband Tyler, “Hey do you want to try that restaurant?” Depending on the situation, that innocuous question could mean any of the following (and usually I didn’t even really know which):
- I really wanted to try it, but didn’t want to make it all about me.
- I was curious about trying it, and was trying to gauge his interest level to figure out our joint interest level.
- I was not interested at all, but I genuinely thought he would like it, and it would be a nice gesture to do something nice for him.
The assumptions we made about the meaning behind what we said caused a lot of miscommunications. After “debriefing,” we would often realize that we had done something that I thought was more for him and I was just tagging along, and he thought it was more for me and he was not that excited about. We would end up doing things neither of us was enthused about, thinking that it would make the other person happy.
I was used to a much more passive communication style, and for me to say, “I want to try this restaurant, what do you think?” felt overly selfish and demanding. When Tyler would say “I want to do X, what do you think?” I thought the decision had been made, and I was being informed — so I would agree begrudgingly. It took awhile for us to figure out that his intention was just to be explicit about what he wanted, and hear what I wanted, so we could make a plan accordingly. Even when I would say what I wanted, I was already making a lot of compromises based on my assumptions of what he or anyone else would enjoy or want — most of which were probably wrong.
Don’t fall for these traps
What makes it so hard to just say, “I want _____________.”? End of sentence. No buts, no disclaimers, no context.
It turns out I’m not the only person who has struggled with thinking about what I want in a very limiting way. Gaining clarity and being explicit about what you want doesn’t mean that you expect to always get it — this is where I used to, and still sometimes, get stuck. It feels presumptuous to think only about my needs and want, and it feels counter-intuitive to a lot of my social conditioning to be collaborative and helpful. It’s a trap because my efforts to be selfless backfired many times. This is what I call the altruism trap, and I’ve fallen for it many times. In the example with my husband, I was not explicit about what I wanted, which led to layers on layers of implicit assumptions in our communication that caused frustration and confusion. Often, the most helpful thing you can do to help those around you is to be explicit both about what you want, and also your expectations for getting it.
Another trap is the limiting belief that you won’t ever get what you want. Who am I to aspire to that? And by saying what I want, if I never get it, I’m a failure. This is another one of those sneaky pranks our inner critics plays on us. It’s a self-fulfilling cycle — if you never let yourself think about what you want, you certainly won’t ever get there (because there’s nowhere to get to), and your inner critic says smugly, told ya so. When you are honest with yourself about what you want, you start to take actions and next steps that move you there — and when you tell people around you, they can help you get there too.
Permission to think about myself
A few years ago, my manager asked me to write up some 6-month OKRs. I don’t have enough context on what’s needed for the company, I thought. How can I plan 6 months out when the strategy and teams might change? I want to build more technical depth, but we probably need me to do more management and hiring. Ignore the company’s needs for this exercise, he said — just think about what you want. Imagine that every opportunity is open to you — what do you want?
When he posed this question so explicitly to me and gave me permission to think only about myself, for this brief exercise, I gained clarity on what it was I wanted. And I realized how infrequently I think about what I want. Unintentionally, I would typically factor in the company’s situation, what I think is possible, what I think is needed from me, and what I think other people want me to do — and from that place of many constraints, I might say what I “want.” I may have had an inkling of what I wanted, but it was never fully developed or written down — I expected other people to tell me what I was good at, and give me more opportunities to grow.
Helping others help you
Sometimes what you want and what a company needs will be well-aligned — maybe even 95% aligned! Amazing! But usually it’s more around 25–75% (I made those numbers up). If you don’t know what you want, you may just stay at a company just living with a growing sense of dissatisfaction quietly, hoping that something changes. If you know what you want, you can have more explicit conversations with your manager or peers around you. And it’s not a threat — you’re doing them a favor! You’re telling them how your current work aligns with your values or goals, and exactly what you need to stick around longer-term.
Leadership coach and friend Jen Dary writes, “Retention is a communication strategy in which both sides find new ways to CLICK; managers are at the epicenter of this work.” Managers are often hesitant to ask direct reports what they want. What do you want to work on? What do you want that you’re not getting right now? What do you want? A lot of times, this reluctance is because it feels like if you knew what people wanted, you would have to give it to them. Otherwise you are mean. Or it can feel like a luxury to think about what people want — too many deadlines, too many features to build, how could we possibly think about what people want?? But if you know what people want — ignoring company needs — you are much better equipped to motivate and retain them. And instead of hoping people are happy when they are actually taking sick days to interview at other companies, you can have honest conversations about how much their current work aligns with what they want. An added though somewhat unfortunate bonus is that managers who truly try to understand what their direct reports want are so few and far between that you will end up retaining your team for far longer than if you didn’t try to understand at all.
Six months after drafting my OKRs, my manager and I pulled them up in a 1:1 and both realized that I had taken on a lot more engineering-team-wide organizational work, and hadn’t done a lot of deeper technical work (one of my objectives). The next time a challenging technical leadership role emerged, he said it was mine if I wanted it, and convinced me that even though I didn’t feel like I had enough experience, I was the ideal person to lead the project. The exercise of being explicit about what I wanted — even for an hour twice a year — helped us be much more intentional about my growth, and retained me for many years.
What do you want?
When you try to answer that, you might not come up with anything. For many years, I was successful and progressing in my career even though I didn’t ask myself this question. I didn’t do much planning or goal-setting, and things turned out ok. And that’s probably fine for awhile — a lot of my early years was banking hours spent coding and working with people. There’s so much to learn that I absorbed a lot just by showing up. A lot of the goals I saw around me “I want to be a founder, get into YC, raise a Series A round, and hire employees” — didn’t appeal to me. But what you want doesn’t have to be — and arguably shouldn’t be — so prescriptive. It could be “I want to be challenged, learn new things, and increase my impact in the organization.” Design leadership coach Mia Loira tweets, “Instead of goals, identity the values that are most important for you to live by in 2018 and figure out how you can more closely align with them.”
One of the most powerful questions in coaching is simply asking, What do you want?, and asking it over and over again to cut through the limiting beliefs and fear to help someone gain clarity on what it is they want.
The photo at the beginning of this post is of Singapore. Over a year ago, I was feeling very burnt out in the daily grind of commuting to SF and being a mom to a 1 year-old and 3 year-old. Any vacation I could imagine with two small children would be more stressful than going to work. My husband asked me what I wanted, and I threw out a few ideas, one of which I thought was impossible — to visit my friend Winnie in Singapore for a week. This went against every preconceived notion I had of being a mom, being a responsible parent, being a good partner. In a very matter-of-fact voice, Tyler said, “Ok, so book tickets. Go to Singapore.” A few months later, I went to Singapore — and came back a week later feeling refreshed and a far better mom and partner.
We need to have more explicit conversations about what we want — first with ourselves, and then with others. If we can’t speak explicitly about what we want, we can’t be honest with ourselves about if we’re making progress, how we find alignment, and how we accommodate others. Advocating for yourself and what you want is a muscle that grows stronger when you exercise it — start with things that are small and frequent, and you’ll find that when there’s something you really want, you can both identify it and make progress towards it.
I’ll leave you with this slight variation: In exactly one year, at the end of December 2018, what do you want to be true?
In 2018, I will be co-leading workshops with Edmond Lau to raise the bar for leaders in tech by focusing on communication, listening, asking powerful questions, and building deeper relationships. We will be bringing everything we’ve learned from our expertise working at startups and large companies and coaching leaders in tech. If you’d like early access to workshop opportunities, leave your email here.
