Delegation Mini Series: Part 3: Delegation - “Seeing Around Corners”
I have coached startup founders and leaders since 2011 and in this time I’ve seen enough patterns that I can draw on those experiences to help current clients “see around corners.” Here are six additional gems of delegation wisdom I’ve gathered over the years:
1 - There are going to be things you should not delegate (even if you want to).
Although I am mostly coaching on how to manage your own psychology to relinquish control in order to delegate more, I want to acknowledge that there are going to be decisions, responsibilities or tasks that you should never delegate to others. This list may evolve and change depending on your company’s stage and your role -- but there will likely always be at least a few things on this list. A few examples:
One CEO I know never fully delegates decision-making around: (1) executive / C-level hiring and/or (2) any issues where she needs to translate pressures from the outside world (e.g., BLM, #metoo, COVID-19 vaccinations, recessions, etc.) to her employees who are hungry to hear from leadership on how the company is interpreting and responding to these events.
During early-stage growth, it might not be ideal for a founder-CEO to fully delegate Product or Sales if a founder’s unique skillset in product innovation or sales conversion is the “special sauce” needed to grow the company to the next stage.
I sometimes see founders over-delegate “leadership through a cultural challenge/crisis” to a Head of People which both handicaps the People Leader’s ability to address the problems effectively and can create a dysfunctional dynamic when the founder’s behavior may be part of the root problem.
It’s important to articulate this list for yourself and keep it up-to-date for two reasons: (1) it helps your direct reports know what boundaries exist and when they should always involve you (e.g., below the waterline issues; cultural challenges; etc.); and (2) it will help you to hold focus on that area even if the work involved is time-demanding, boring, stressful or something you’d otherwise prefer not to do.
2 - There is a difference between delegating tasks and delegation decision areas/cognitive load.
Sometimes startup leaders tell me they have competent teammates in place who they’ve successfully delegated work to, but they still feel fragmented and overwhelmed. What’s going on? In these cases, I inquire whether they’ve delegated a task (“Hire two engineers for this team.”) or delegated a decision area. The decision area is the “cognitive load” that someone carries, a load that would drive them to identify that task (and others) in the first place. (“You’re in charge of leading, growing and managing the engineering team to make sure we can hit our company goals.”) You may have a team of people in place executing on your assignments, but if your company is scaling and you aren’t intentionally delegating more and more decision areas/cognitive load over time --- you will eventually overwhelm yourself with too many decision areas to hold in your head. This is a simple but powerful frame to share in 1-1s with your teammates who are ready to take on more responsibility -- in what areas of their role could they “up-level” to being delegated decision areas by you? Only when you’re delegating decision areas (in addition to tasks) will you fully experience the freedom of taking cognitive load (not just work) off your plate.
3 - Delegating to an assistant, to IC-level reports and to C-level executives will look quite different in practice, even if the list of factors you consider is the same.
Whether you’re delegating a small admin task to your virtual part-time assistant or delegating a P&L level responsibility to a new executive, the five factors below are what to consider when you are first starting out a new delegation dynamic or when you are struggling to delegate effectively. Some of these might be questions you answer on your own through inference, observation -- others you might talk about explicitly with the other person.
Me - What is my psychology around delegation? (my reflexes/defaults; my past success and failures with delegating; how I might project my own learning/training/work style)
You - What is your psychology around delegation? (your comfort or familiarity with tasks or areas I am delegating; how you reflexively respond to that level of comfort/discomfort; your inferences or assumptions about delegation coming into this team at this time in this role; your past experiences being delegated to)
Us - What is our current relationship like? (brand new to working together? Know each other, but this is a new role/new phase/new org structure? hitting a reset after some bumps (re-org, layering, new manager, PIP, re-scoped role; what level of trust exists?; given our respective psychologies around delegation, do we know where we might collude or have friction?; power dynamics that might block communication or delegation?)
The Work - What is the nature of the work being delegated? (Is it a task or a decision area? How critical is what is being delegated? Is this new for company or just new to the person? What is the degree of complexity? What are the risks in delegating this?)
The Context - What is the situation or context surrounding the work being delegated? (What level of pressure is the company facing? What constraints are we operating under? What context needs to be understood to successfully complete the work and how will that context be shared?)
The way you answer these questions (and, subsequently, the level at which you delegate) will vary depending on the person you’re delegating to (their work history, role, seniority, experience) but the underlying questions to consider are the same. The more reps you can get in working through these questions, the more you can cultivate your delegation instincts and reflexes to assess these questions every time you need to.
4 - Delegation is both enabled and limited by trust, so it’s important to understand how trust is built (and broken) in order to delegate effectively.
Trust can feel monolithic and loaded to talk about, but if you can break it down into its underlying components you can make it something that can be explored and talked about between teammates, co-founders or managers+reports. If you notice that you are reluctant or struggling to delegate because of some loss (or absence) of trust in the other person, read more about the underlying components of trust in Build Trust By Breaking It Down. And then take steps to build (or rebuild) the trust in order to engage more fully in delegation.
5 - The return horizon for delegation is sometimes further away than you anticipate. It’s tempting to give up along the way. Don’t.
Sometimes the “freedom” startup leaders of growing orgs are hoping to find through delegation can feel like a desert mirage. I imagine it as three consecutive valleys of pain that you must walk through. It can help to expect the valleys (and know there are three!) so that you keep going rather than abandon the journey mid-way.
The first valley of pain is when you are overloaded, fragmented and don’t have a person to whom you could delegate tasks or decision areas. You get out of that valley by deciding to hire.
The second valley of pain is when you are spending the time and energy to hire someone. It’s exciting but painful because you still have to get the work done, while also taking on additional cognitive load to decide who/how to hire (often time-consuming!) and then actually hire them (always time-consuming). But once you’ve made the hire you turn the corner and expect freedom land, only to find the third valley of pain!
The length/duration of this third valley can vary greatly, but this is the pain of when you’ve hired someone and you’re even more exhausted because you’ve been doing the work and the hiring for weeks (or months). It can be tempting to just throw your new hire in the deep end and hope they swim. The third valley is that initial phase of onboarding & training & expectations calibration and it lasts much longer than just the days or hours you’ve set aside for “orientation.” You will feel like you are spending a lot of time (maybe too much time) but if you’re spending it effectively it will help you emerge from that last valley. And maddeningly, if you try to bail prematurely or find a shortcut out of the third valley, you usually make the trail longer and decrease your chances of ever finding your way out.
So, don’t forget about the third valley on your way to Delegation Freedom. Save some fuel (energy, attention, bandwidth, time in your calendar) for that part of the delegation journey.
6- You can learn about delegation from many sources outside of startups or even outside of business.
Delegation is, quite literally, how our human brains are built. For example, as our toddler brains develop and we master physical skills, like balance or walking, our brains “delegate” control of these functions from higher to lower neural centers. (In neuroscience this is the process of “relegation” to create “automaticity” and free up our ability to achieve higher-level cognition over our lifetimes.)
You can also find wisdom or inspiration for how to delegate more effectively from: school teachers, honeybees; parents; moms; and even the Bible. In any system that needs to grow or requires some form of coordination to function, you will find delegation. So, stay alert--you never know when that next gem of wisdom will reveal itself to you and help you see around your own delegation corner.
Anamaria
