To survive the graveyard of failed businesses, a startup has to move fast. One aspect of a get-stuff-done environment is that there will frequently be a boss—often our manager or an executive—who needs us to get something done urgently.
Then, we do the task, and our boss says, "that's not quite what I had in mind." Or, they heavily edit the work, and it feels like they created a new document. Or, we skip our friend's birthday party to finish and are told, "oh, I didn't need it till Friday."
In each case, we may feel like the task was a waste of time.
If this was a Tony Robbins intervention, he would likely say we define our purpose and ascribe meaning to what we do—no one does that for us. Maybe the goal is to prove to ourselves that we can rise to the occasion even when it's hard. Or maybe, it's a chance to learn to ask explicitly when something is due. Or maybe, it's closer to what it often is for me, an opportunity to get fast feedback and see someone else's exceptional example.
Brene Brown—she is fantastic; check out all of her work—offers another tool in her book Atlas of The Heart:
When I hand off an assignment at work, I will often say “Let me paint done”—and if I don't, you can be assured that the person on my team will say “I'm on it. But I need you to paint done.”
“Painting done” means fully walking through my expectations of what the completed task will look like, including when it will be done, what I'll do with the information, how it will be used, the context, the consequences of not doing it, the costs–everything we can think of to paint a shared picture of the expectations. It's one of the most powerful tools we have.
Even if we've never heard "paint done," many of us know we should do that. What often happens is that we don't feel like we have time to ask questions since we need to start working on the task, or we feel uncomfortable asking questions since we think our questions are dumb.
Using philosophies from Tony Robbins and Brene Brown, I detail how to think about urgent requests, discuss expectations with our boss, and remain energized.
Step 1: Don't Automatically Say Yes
If we don't understand the task and it won't be fast, we must resist the urge to just say yes. I'm uncomfortable with silence and biased heavily towards action, so sometimes on zoom or in person, I take a sip of water or stretch to force myself to pause.
Once I'm out of a scarcity mindset, I ask questions.
Step 2: Uncover Strongly-Held Beliefs
Whether we have one or multiple questions, the goal is to understand strongly-held beliefs or what Brene Brown calls "stealth expectations." For example, I used to spend weeks talking to different teams to define a product roadmap, only to have an executive come at the eleventh hour and say we had to include a feature. I valued the executive's business context that I didn't have, but the feedback was energy-depleting due to the timing. Eventually, our team built into our roadmapping process an early meeting with key stakeholders around expectations and began to avoid the last-minute roadmap scramble. In addition, because we knew more business consequences in advance, product managers were more creative in solving the underlying problem and looking for solutions beyond the feature request.
I’ve found the easiest way to bring up stealth expectations is using existing company terminology, or if the language doesn't exist, coining the term by pointing it out. In the previous example, my product team called that roadmapping meeting on expectations "uncovering strongly-held beliefs." That shared understanding allowed me to use that phrase outside of roadmapping for any issue requiring expectation management. When I moved to another team, I started calling out unspoken expectations using statements like, "I didn't realize that was a strongly-held belief. Can you tell me why that's important?" and created processes using that phrase.
Another tactic to understand unspoken expectations is looking for an example or template. An example doesn't just mean asking for a sample slide or written outline. In one case, a new product manager on my team asked to present last during a week of product presentations to the executive team. Presenting last allowed them to see others' meetings and know what to expect. In a similar vein, I often ask my boss how they would approach the task. The goal is to understand their expectations through how they would spend their time.
However, even when we ask the right questions, we sometimes receive cryptic expectations. For example, we all ask, "when does it need to be done?". When our boss responds, "as quickly as possible" or "let me know whenever you can get it done earliest by," we get tripped up. In these situations, I ask more questions before committing to a timeline. I remind myself not to make assumptions about importance since that could lead to missing important deadlines or reneging on time with a best friend.
In addition, even when our boss states the due date, it's our responsibility to voice if that works and will not impact other deadlines and our personal life. Our boss wants to know the impact and won't know it unless we say it. Even though it can feel awkward, it's always worth bringing up.
Lastly, when I am concerned about my questions seeming dumb, I preface them with a phrase like "To make sure I'm not making any assumptions." I appreciate it when others don't make assumptions, and I'm sure they feel the same way.
Step 3: Embrace feedback
Especially if we are new to a role, we likely will be off on whatever we deliver. It's hard for a boss to articulate all their expectations, and it's their job to give feedback based on their experience.
In those cases, it's back to Tony Robbins:
You see, it's never the environment; it's never the events of our lives, but the meaning we attach to the events … how we interpret them … that shapes who we are today and who we'll become tomorrow.
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I love the emphasis on calling out strongly held beliefs early -- the divide between things we know we don't know and things we don't know we don't know is huge.
I hadn’t heard of the “painting done” concept before and while I think one reason people don’t do it is bc of time scarcity I think another reason is that many people (incl me) don’t always stop to really think through what we want and why. It’s a really good reminder that if we don’t take the time to clearly define what the vision is, everybody’s downstream job just becomes harder.