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Delegation and Managing Up
Hello! I’m Aaron Kardell. In this Sunday newsletter, I pick one random topic weekly to go deep on and have some disparate quick hits at the end.
This past week I passed the 100-subscriber threshold. I’m honored that so many of you are following along!
One of my goals for leadership growth this year is to become a better coach and less of an in-the-weeds doer. With my teams, I want to push myself to have more goal-oriented conversations and to be less prescriptive on tasks.
At HomeSpotter, one of our four company values was that we are doers. At Lone Wolf, one of our values is that: “We do the work, big or small.” Both of these resonate with me deeply. At my core, I like to roll up my sleeves and get work done.
At various stages of my career, this trait has served me well. Before I raised funding or had my first employee at HomeSpotter, I needed to do everything.
This has, on various occasions, also been a handicap for me and my teams to grow. I was worst at this during certain stages of the HomeSpotter journey. There was rarely a function of the company that I hadn’t already done a little bit of. It was too easy for me to offer an opinion on every matter under the sun. I weighed in not just on what we should be building but also on how we should build, sell, market, etc.
As a reluctant-to-admit enneagram 8 with some enneagram 5 tendencies, I strongly value independence and doing things my way. While I appreciate how annoying and frustrating these traits can be to others, it’s still hard for me to keep these tendencies in check.
My Predictive Index placard below illustrates how important it is for me to be in the driver’s seat. I’m a terrible natural collaborator.
Self-awareness is the first step. And I think I’ve incrementally improved on this over the last several years. But I’m hoping to really lean in and make improvements this year. My team’s scope of impact will be limited over the long haul if I keep doing things the way they’ve always been done.
The remainder of this post is content I’ve encountered on the topics of Delegation and Managing Up. I’m capturing them here for my own reference throughout this year. I hope you find them helpful too.
Leadership is hard. One of the hardest parts is delegation. How much guidance do you give? When do you do it yourself? When/How to track others to-dos?
As a young leader, I wish I had a cheat sheet for delegation. So I wrote one.
Abdicating and Micromanaging Are Both Problematic
First, the biggest delegation mistake I see leaders make: either 'abdicating' or 'micromanaging.' Abdicating is when you hand over a task/responsibility and disappear assuming it's getting done. Micromanaging is directing every little thing your report does.
Which do you do? Probably both!
But that depends on:
1) The persons seniority.
2) Their level of skill for a given task.
3) The situation at hand.
The two tools I use to help me do this well:
Ladder of Leadership (LL) and
Task Relevant Maturity (TRM)
Ladder of Leadership
Consistently meeting your team where they are and helping them stretch is key. It becomes easier when there is "common language" the whole team can use to signal this to each other. The Ladder of Leadership solves this!
When a CEO meets their board, they tell them "here's what I've been doing" (a 7) and I'm about to (5). When an entry level person starts as a waiter, they say "tell me what to do." Everyone else sits on in between on "rungs" of the ladder.
For an IC or MM to get promoted: Look at your last 10 emails to peers or senior people. Now jump up 2 rungs in your next 10 emails. If you've been asking "what do I do?" start saying "I think I should,” instead of "I see" start saying "I recommend." Watch your career soar.
Now let's flip to the manager:
You're an expert twitter🧵 writer and starting a twitter agency. You are a 7. You hire an entry level person and it’s not working out. You've been managing them at the 5/6 level asking "what did you do?" Instead, they need you at the 1/2 level: "do this."
Now.. Ensure they consistently deliver what you tell them at "level 1."
I call this the 'triangle of success': do they deliver what you asked, on time and above the quality bar indicated? Once they do, start to stretch them! Ask what they think. Ask what they recommend!
Inviting your reports to move up the ladder gives you leverage and helps them grow. It’s the ultimate win win.
Task Relevant Maturity
"But Jesse, I hired a VP and managed them at 5 and it didn’t work!" "I hired a new VA managed them at a 2 - they quit!"
We can take it to the next level with TRM. It turns out very senior people can be total beginners for some tasks. On the flip, junior people may be didn’t experts in specific tasks. The key concept here is: Task Relevant Maturity.
TRM is a simple concept with a long name: how well does the person know how to do the task they've been given? Every single person is at a different place in their development. And that development level is unique for each and every skill!
e.g. I am an expert in growth marketing - I could easily fly at level 6/7 and just update people on what I've been doing. I am a total beginner in setting up a 3PL - someone tell me what to do! If someone senior or mid-level isn't delivering, ask them about their TRM!
Communication is Key
The key to making this work in a fluid way is to make talking about the LL and TRM a normal part of everyday work discussions.
Examples of what this will sound like: "Jump up on the LL and make a recommendation!" "I'm new to TikTok. Can you jump down the LL for me?"
The last item on the list is "the situation." At times, there's an opportunity so meaningful that the leader wants to operate with total control. This is rare and temporary (~1/year). Communicate it clearly to your team. Then follow daily check-ins and be hands on.
So to review the secrets of delegation:
Learn and study the Leadership Ladder and Task Relevant Maturity.
Make both normal vocabulary in your organization.
For any given task, discuss the persons Task Relevant Maturity and agree on where you both want to be on the Leadership Ladder.
Stretch people by jumping up 2 rungs.
Make space to calibrate/grow.
I love that Jesse gives examples of how managers can level up their asks and how individual contributors can increase their contributions. I hope my teams and I can adopt learnings from the Leadership Ladder and Task Relevant Maturity this year.
An unlock for this to work is that even within the Leadership Ladder model, you need to allow your team to do it their own way, learn, and fail in the process. Their chosen way often won’t be your preferred way. Back to the whole enneagram and Predictive Index self-reflection above – this is really hard for me. But I’m going to work on it.
I have a different take on what Jesse calls “The Situation.” While I certainly see cases where those situations could be sparked by opportunities, most examples I’m aware of are prompted by a major crisis. When COVID hit, we saw revenue from one segment of our business drop precipitously overnight. In that case, I outlined with my competent and senior executive management team that I was taking on what Ben Horowitz refers to as a Wartime CEO stance. I temporarily embraced getting a lot more prescriptive with everyone to weather the storm. I was explicit that this was for a limited time. However, operating like this only works if it’s the exception to the rule.
While better delegation is something many leaders need to work on, everyone can improve their skills in managing up. Even CEOs have to manage up with their board or sometimes their customers.
Most people suck at managing up. They waste their bossʼ time with too much (or too little) information. Hereʼs how to give the right amount of context:
Star employees are exceptional at communicating and managing up. This is even more important in a remote working environment. They proactively communicate to show theyʼve got it handled and prevent endless one-off questions.
If you donʼt share enough context, youʼll waste time on:
❌ Needless back-and-forth
❌ Avoidable follow up questions
❌ Misunderstandings and confusion
Here are 8 ways to give your boss the right amount of context:
1. Remind them where you left off.
Task switching takes a lot of energy. Your boss is probably reading your note in between meetings (or during one!). Assume theyʼre reading with partial attention. Remind them where you left off so they can task switch faster.
🚫 “Hereʼs the updated link.”
✅ “Hereʼs the updated pitch. I incorporated your feedback & included a change summary below. Let me know if you have any questions. Iʼll plan on shipping tomorrow morning.”
2. Be specific & explicit about what you need.
Donʼt assume your boss knows what you need from them. Be specific about what you need and what the next step is. Otherwise, theyʼll assume youʼre making progress and will be surprised to find out youʼve been stalled for weeks.
🚫 “The new ad is updated in the Google Doc. Itʼs published in FB, but not running.”
✅ “Please approve the new ad copy (screenshot below). Once you approve, Iʼll publish and go live on FB.”
3. Mention if itʼs an FYI.
Donʼt make people guess if they need to take action. If your recipient has to follow up to ask, it slows everyone down. Folks think theyʼre being helpful by forwarding a random email. But without context or next steps, these messages are useless.
🚫 [No context]
✅ “FYI. Sharing because you mentioned wanting to see examples of investor updates.”
4. Adopt an action-oriented posture.
If youʼre stuck, donʼt just stay stuck. Speak up to get what you need to do your job.
🚫 “I didnʼt do it because I donʼt have the right permissions in Google Analytics.” ✅ “Can you add to me to Google Analytics with x permissions? I need it in order to do y.”
5. You can share less context when…
✔️ Youʼve made this type of decision many times & you have task relevant maturity ✔️ Decision is reversible and inexpensive
✔️ This is top of mind for your boss (not one of 25 projects theyʼre managing)
6. Aim for more context when the decision is…
✔️ Irreversible and expensive
✔️ Youʼre making this type of decision for the first time
7. Mention your criteria and assumptions.
Most bosses want to know that you did your due diligence and are thinking ahead. Show your thought process. Your boss can point out gaps in your logic or update the criteria/assumptions you used.
🚫 ”I recommend this platform.”
✅ “I recommend this platform because of x, y, z criteria. My assumptions were a and b. The potential trade-off is x, but seems manageable because y. I vetted options, including [insert options] but [my recommendation] better fits our needs.”
8. Put the recommendation at the top, then context below.
Leading with a recommendation allows your recipient to read as much or as little of the context as they need.
🚫 [Actions, backstory, and context all jumbled together]
It's your job to do the heavy lifting. By providing the right amount of context, your boss won't have to guess to figure out what youʼre trying to do. Take the mental load off your boss & youʼll shine as an employee. Win-win.
I’ve read both of the following books, but I plan to re-read this year:
High Output Management, by Andy Grove. He covers Task Relevant Maturity amongst so many other things. This is the top resource Ben Horowitz cites for improving management skills. (For many years, this wasn’t available on Audible, but it is now!!)
Measure What Matters, by John Doerr. The original book on OKRs.
What other resources do you recommend I look at to improve how I think about delegation and team empowerment?
Special thanks to Caroline, Joseph, and Jesse (not Pujji) for conversations this week that helped inform this week’s topic in several ways. And thanks to Wes Kao (@wes_kao) and Jesse Pujji (@jspujji) for always creating great content. Check out and subscribe to their newsletters: Wes Kao’s Newsletter and Jesse Pujji’s The 3-1-4. And for more management insights, consider subscribing to Tim Wilson’s Acuity Leadership Group Newsletter. He brought Wes’ insights to the forefront for me.
This Week’s Quick Hits
I have a colleague I’ve worked with looking for work in residential real estate technology. He knows the industry incredibly well. He would be a valuable asset to anyone looking to refine and improve their go-to-market strategy, amongst many other things. Want more info? Reply to this message, and I’ll share some details.
Have any travel recommendations for Japan or Western Europe for a family of 4? I realize that’s a broad question, but I’m curious to get your feedback.
Teslas are now actively encouraging eligible owners to opt into the full self-driving (FSD) beta on the main screen. I previously shied away from opting in when it took more work. I’m a late early adopter on many things. The “good driving” qualification criteria necessary to get the beta were high, so I didn’t even try. I’m now using it to drive me on many more city streets, and it’s completely fascinating. It’s doing a way better job than I would’ve anticipated. It drove our family home about 7 miles (over half on city streets) today, with no interventions.
In other Elon Musk-led company news, I was disappointed that Twitter cut off Tweetbot and other third-party apps. It did not inform those apps or companies of what was happening. As this week’s post demonstrates, I learn a lot from others on Twitter, and I find it somewhat unusable through the main app. I bet Dick Costolo, former Twitter CEO, is laughing. He tried several ways to kill off third-party apps and got a ton of blowback. Just another sign that revenue is in massive decline. My days remaining on Twitter may be limited. It’s a shame. It’s unique amongst social networks in its ability to curate learning and newsworthy information.
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