Being Hired to Care
What work looks like when you’re invited into the mess.
“We have our first board meeting next week, and I’d love to get your take on a few of the slides.”
I’d never been to a board meeting. I’d never run a startup. I’d never had to raise money from investors. In some ways, this request felt totally out of left field. But in other ways, it was exactly what I was brought on to do.
One of the biggest mistakes that I see people make as they start to dip their toes into advising is try to anchor their work to specific deliverables. Doing this is bad for a number of reasons, but the primary one is that when you’re being brought on as an advisor, you’re not being hired to deliver anything, you’re being hired to care about a company. You cannot do this well if you’re constrained to a single lane or output.
Throughout their careers, most people make a shift from being hired for activities (“do x”) to being promoted into roles where they are hired for outcomes (“help us achieve y”). As an advisor, you move another level up in altitude and drop the second half of that sentence.
Over the last few years, I have been fortunate to be hired by founders and leaders to care about their businesses. I'm writing this post for others who are in or near that position because it feels unnecessarily opaque to people outside of the work.
There are no playbooks. You have the opportunity (and obligation IMO) to bring everything you have to the work — your skills, your opinions, and your whole self.
What this looks like
In "Me-As-A-Service" I sketched out different "ways of being" that show up in my work, depending on who I am in service of and whether or not I'm accountable for deliverables.
I went on to talk about how those different ways of being show up together and said:
"As much as I am putting shape to and labeling potential ways of being, my honest experience is that most of these ways of being are the front door to deep, meaningful partnerships with people which morph and co-occur over time. I believe there are reasonable downsides to sku-ifying yourself, especially if you’re like me and appreciate getting invited into the mess... I often evaluate the success of any of my work by the degrees of freedom with which I’m given to engage with people besides my primary point of contact. The more that I’m trusted to do the work around the work without having to pre-define it, the more successful and impactful an engagement is."
Being fully invited into the mess is how you know that you're being hired to care. [1]
While you're often given a starting point, you're rarely given a lane to stay in. The expectation is that you will help both where others know you can and where you yourself see an opportunity. This lack of a single lane can be both disorienting and empowering. As Tom Critchlow points out, “Both deadlines and deliverables are designed for legibility - for the control and measurement of work - not for effectiveness” (emphasis his). When you’re hired to care, effectiveness is your north star.
Because you're hired to care, you're trusted to be mostly autonomous in how you operate (my father refers to this as being "closely aligned and loosely coupled"). This is especially true when it comes to diagnosing what's wrong and identifying the best paths forward (if not addressing them directly). To do this well requires context, which is why I ask for full Notion and Slack access (or similar) when I start working with companies. I want to reduce the amount of time I'm waiting for someone to approve my access to something and maximize the amount of time I can spend actually working on the most important thing.
The empowering aspect of this is that without a lane or a specific role that you're supposed to play, you can draw from your full toolkit. This quickly shifts you from playing sheet music to jazz:
Bring in some of the exercises from your workshop last month as a discussion prompt
Walk the team through a few slides from a recent talk that's relevant to this problem
Pop into Metabase and figure out what retention actually looks like for recent cohorts
Grab time with the head of partnerships to get clarity on what slide 47 was about
While I'd argue that all of these things are always on the table, when you're hired to care you have to trust yourself a bit more and ruthlessly prioritize what you believe will move the business forward, since people will rarely specify how you should contribute.
The Iceberg Problem
One of the biggest challenges I've come across in these open-ended configurations is the iceberg problem — where clients are only aware of your exposed surface area, though the real value comes from what's below the surface.
Doing this work well means that you have to balance pulling from what's below the surface without spending too much time pointing at or talking about it. I have rarely told my clients the names of past talks or what the overall topic is, but I share past slides every week with clients because they are relevant and useful to the topic at hand. When I meet with that client I mentioned at the beginning, they’re disappointed if I don’t have at least one diagram or slide related to what we’re discussing.
Some friends who do this work spend too much time talking about what's beneath the surface rather than using it. Talking about them, rather than applying them, can exhaust your audience cognitively. Your client shouldn't have to connect the dots between how a training for their team will help solve the problem at hand, and you should never expect them to know or pull from your full catalog or toolkit. That's your job.
Aren't executives hired to care?
"But Behzod, executives are hired to care! You're describing the role of a CXO."
Yes and no.
You're right that a C-suite's job is to worry both about their discipline and often adjacent ones (at least in terms of interactions). But they are loosely bounded by those disciplines. And more importantly, their success is often measured by the specific metrics they are accountable for (related reading — Tom Critchlow on executive dashboards.)
Part of why advisors are so valuable and different is because they are not beholden to any specific team or role. They are not a part of the machine — they sit outside of it and maneuver through it. They are brought in to focus their time and energy on the highest leverage things that will move the business forward, and they do so without dropping the ball in a critical area of the business.
Being hired to care, in my experience, is boundless. You aren't just caring about one department or one part of the product and your success is not measured by just one metric going up. You should care about the entire business and everything it touches. If you don't have an in-road to a team or area, you carve that path or build that bridge. As soon as you let an org chart stop you, your value has already started to diminish.
Thank you to Tom Critchlow and Elan Miller for our ongoing conversations about these ideas and providing feedback on drafts of this post.
[1] Elan Miller talks about why he runs towards drama, highlighting how “a lack of clarity is usually what’s holding [clients] back. Embrace the mess!