Summary

Delegation shouldn't feel like throwing work over a wall and hoping for the best. Laila's approach transforms delegation from a task handoff into a strategic setup—where both you and your team know exactly what success looks like, when to check in, and how to course-correct before things go sideways. The result? Less micromanagement, fewer last-minute scrambles, and a team that actually runs.

What’s in it for you:

You're an "I can do it" person struggling to let go (even though you know you should)
You keep getting pulled back into projects you thought you delegated
You're trying to figure out how to be hands-on without being a micromanager
You want your team to take ownership—but you're not sure how to set them up for success

Helia’s Perspective

CLARITY goes so far. It's all we ever want to give, and yet we fall short way more often than we'd like to admit. I'm a little embarrassed to say I don't think I would ever fill out Laila's delegation template (below!!) to completion (which is exactly why I asked her what's the ONE thing we need to do). But everything she said made sense—for the manager, for the team member, for the organization. When things are shifting and we want to ground ourselves in where it started. When we want someone to be able to run and make things happen. The idea that you can spend 30 minutes with this and give folks what they need for things to actually work? Music to my ears.

I also LOVE that this is a way of using a decision-making matrix (like RACI or RAPID) that might actually work. I've tried…and I’ve never successfully integrated one across an org or department as a whole. There are just too many nuances and shifts and possibilities that mean it's constantly getting revisited. But outlining potential decisions in a project? YES!!!!!!!

Again, I'm not sure I would use the template in its entirety every single time. But when I think about what I want for my workplace, for all workplaces, for everyone I work with, and who I want to be? This. Exactly this.

Laila’s Story

"I think of myself as a setter," Laila told me. "Like in volleyball, a setter. I was a setter in high school and I was never great. But I loved the role because what I realized is I could get to know my team really well and I could set them up to make the spike in a way that was so fulfilling."

She learned who liked the ball close to the net and who liked it far. She figured out she could call on the person in front while knowing the person behind would be just as ready. "This is who I am as a professional. I have built my entire career figuring out, ‘Who do I set up next? How do I put each person in just the spot they want to be so that they're making the spike?’”

Laila Plamondon is now the Senior Director of IT at Uncommon Schools, where she leads a team of 20. She's brilliant at technology, but what she loves most is coaching and managing people, project management, and communication. "I honestly wake up every day interested and excited to tackle whatever we have on our plate."

When I asked what she's proud of, she didn't hesitate: "I am really proud that I have had direct reports who were promoted into my roles. So I've had a direct report who became my peer, then direct report and then peer again. I'm really proud of the fact that I'm not just making moves, but bringing my team with me."

*Laila and her colleague, Anna Jessup, who I once managed who now manages and facilitates alongside me*

But here's the thing about being a good setter: you have to know what's happening. You have to be clear about the play. And for Laila, delegation is how you make sure everyone actually knows the play.

"I know that I haven't delegated well when I see that there's a boomerang or a bottleneck effect," she explained. "If tasks keep coming back to me or details keep coming back to me for a decision, I know that I haven't delegated holistically because it's causing me to be the bottleneck again."

When asked when someone should use her delegation process (size or scope of project, level of team member, stage of work), her answer is simple—"I have never regretted spending the time on creating a delegation AND I have often regretted not having the delegation." Aka—just do it!!!!!

What this looks like in practice

"You start by asking yourself, ‘What are the outcomes I’m looking for? Like, what does done look like? What is the end result?’"
For Laila, especially as she manages IT project managers, she has a starting list for every project: stakeholder management plan, risk register, decision log, issue log, communication plan. But she's also looking at the end goal of the project itself.
"This section often is the majority of the document. Even though it's one little question, when filled in, it can be the whole first page."
Why this matters: You can't delegate what you can't describe. If you don't know what done and quality look like, your team definitely doesn't know!
How to replicate: Before you delegate anything, write out what "done" actually looks like. Include the goals, the deliverables, what success means. Be specific. And yes, this might take a whole page—that's exactly right.
Why this matters: Instead of "We've always done it this way," you start asking "Is this the right vehicle for where we're trying to go?" Kate uses this to help organizations think about "not only who needs to be on the bus but also what kind of a bus do we need? And is it a bus at all? Maybe we need a jet plane to get where we are going. " She also helps them consider whether they're trying to solve complex problems with broken-down vehicles. She hears leaders articulate a compelling vision but it’s not aligned with the business model: " I hear organizations proclaim, ‘ We're going to solve homelessness.’ Yes, of course, let's do that. That's necessary. We need that. We need people to be housed, but we're not going to get everybody there on your little scooter." And sometimes the solution is collaboration: "If you've got multiple organizations with multiple little scooters, what happens if you all pool your resources and buy a big old bus? Now we might actually get somewhere."
How to replicate: Take time with your team to literally draw this out.Think of it like planning a road trip. Kate suggests making a visual map and asking: "Where are we today? Where do we want to be? How fast do we need to go? And who do we need to bring with us?” Once you have all the pieces laid out, it’s time to ask: What kind of car are we driving right now?" Organizations often come up with illuminating examples—"Maybe we're slowly making our way there in my aunt's 1995 Corolla. It’s cozy and familiar which is fine for getting around town but it's not trustworthy enough for a longer road trip. Maybe it would be better, faster to take a bus or a train.” Once organizations see this visualized, it’s easier to ask the question “What kind of a car, or structure, do we wish we were driving?”
Most managers stop at explaining why the task is important: the context, the problem to solve, why it's urgent. Laila takes it further.
"A next level that I like to include is why this particular direct report is the right person to do this job. Sometimes it is squarely in their job description. Sometimes I've seen them use communication skills that we could really benefit from in this project, or they have the ability to think strategically about this year and three years down the line."
Why this matters: When people understand the bigger picture AND see how their specific skills fit, they show up differently. They're not just checking boxes—they're bringing their best.
How to replicate: Answer two questions:
- Why does this work matter to the organization/team?
- Why is this person specifically suited to tackle it?
Critical note: "To make this work, you can't also have a RAPID for the org. It gets too confusing. You need a RAPID for each project + decision you’re expecting." (Note - Helia agrees!!!!)
Laila also introduces the iron triangle here: time, budget, and scope at the corners, with quality in the middle. Then she tells her team her bias for each project: "I could say time is everything. I need this in my hands by Tuesday. I don't care what it takes you to get there by Tuesday. It can be B+ quality, but Tuesday is the end goal."
Or: "I suspect you're going to get halfway through and then determine that you need more hands on this project. I will get you resources and people power. I need to know by X date what you need. Money is not the issue here. It's high quality."
"My being clear about that upfront gives the owner of the work a much better sense of what I'm expecting and where I'm willing to give and take."
Why this matters: This opens lines of communication. It prevents the endless ‘Should I decide this or check with you first?’ back and forth. It gives permission to ask for what's needed.
How to replicate:
- Think through major decisions that will need to happen. For each one, note who will recommend, who needs to agree, and who ultimately decides.
- Get honest: What do you care about more on this project—deadline, budget, scope, or quality? You probably can't have all four at 100%. Tell the person what you're willing to flex on and what you're not.
"Think about the skill and the will of the person that you're delegating to when determining whether you're going to be hands-on, hands off, moderately hands-on."
Laila maps it out: high skill (they've done this before, know the tools) or low skill (new to them, there's a gap). Then high will (engaged, excited) versus nervous/uncertain.
If someone is lower skill on the project and/or nervous and uncertain, Laila is very hands-on. “We're actually going to do the first hour of work together and then I'm going to send you off to do the rest. And because I have laid this out clearly AND modeled it from the very beginning of the delegation, it's not a surprise to my direct report when I say, 'Hey, I want to work on this together.'"
When she's relatively hands-off? When someone has done this over and over, their will is high, and they're ready to jump in. "I'll say, 'I want you to run as fast and as far as you can. These are the deliverables I expect to see. I will pull you back if I see anything that needs pulling back.' That's my aim for everyone on the team."
Beyond the skill and the will of the delegate, you must also consider the importance of the work. The key is matching the level of feedback to what the work actually needs. As Laila notes, helicopter management often happens when there's a misalignment in the level of feedback and the importance of the work. “If you're doing line-by-line edits on an internal deck for a small team meeting when someone has high skill and high will, that's a mismatch. But if you're doing detailed edits on a board presentation and haven't communicated why it's important, that's also a mismatch—just in the opposite direction.”
Why this matters: This prevents the micromanagement trap. You're not hovering because you're unclear about when to check in—you've already decided upfront what this person needs. And, you’ve communicated that!!!!
How to replicate: Before you say ‘Just run with it,’ honestly assess: Do they have the skill? Do they have the will/confidence? Match your check-ins to where they actually are. Tell them up front what level of involvement to expect. This single conversation prevents weeks of you wondering if you should check in, and them wondering if you trust them.
Laila also notes: "This is also where I try to put all the resources because sometimes that's the place where people get stuck—they just don't have the links they need, the boards they need, the context they need." Make sure they have what they need to actually do the work.
At the end of the delegation conversation, Laila asks: "On a scale of 1 to 10, where 10 is completely confident, how confident are you in your ability to complete this work by the due date?"
"The number doesn't mean anything. It's really about the gap that they see."
Most people say 8 or 9. "And then I'll confirm, so I'm hearing there's nothing else I could provide you in order to ensure that you're successful because I really want you to be successful at this project. This usually prompts them to think of one or two more things that would set them up for success.”
Here's the brilliance: "Then, when you hit all the triggers (you are getting pulled into work, ownership is being dropped), you pull up this document and you say, 'Remember when you said you were at a nine? Now let's take a moment to think about, what could we have done to set you up better? Do you have feedback for me? Was I unclear? Or is this a skill gap that we have that we need to work on?' This allows you to have that conversation that you really can't have without it documented."
And in performance situations: "In the case where you have someone on a performance plan, I believe you need to have a delegation for every single task in that performance plan and you need to get to the point where they are at a nine and you've documented that you have given them everything that they need."
How to replicate: End every delegation conversation with this question: "On a scale of 1 to 10, where 10 is completely confident, how confident are you in your ability to complete this work by the due date?" Listen to the number, but listen even more to what would get them to a 10. Close those gaps right there. Document it. When things go sideways later, come back to this moment to learn together.
Laila also includes two other elements in her template: ‘When to escalate issues’ (where could this go wrong and how soon do you want to know?) and connecting the delegation to ‘Which skills will you have the opportunity to work on’ from annual reviews or professional development goals.

Takeaways

If there's one thing you should do: Just delegate!!!! If you’re not the type of person that would usually fill out Laila’s entire delegation form, put a timer on for 15 minutes, pull up the blank template, and go as far as you can. "The conversation where you share this document will bring out where there's confusion, which is what you're actually looking for. You're much better off having spent 15 minutes on this than not doing it at all."
The guiding principle: "I have never regretted spending the time on creating a delegation and I have often regretted not having the delegation." Remember: "The delegation is a tool, not an outcome—you don't need to get to perfect."
Signs you need to (re)delegate: Tasks boomeranging back to you for decisions, quality issues, last-minute scrambles, you're helicopter managing, or hearing ‘You never told me I had to do that.’

On avoiding micromanagement: The root cause is usually "a misalignment in the level of feedback and the importance of the work"—or not being clear upfront about your level of involvement. When you name your expectations in the delegation (I'll be hands-on for this, hands-off for that), it stops feeling like surveillance and starts feeling like support."

Questions to ask yourself

When was the last time a project I thought I delegated boomeranged back to me? What was missing in the original conversation?
Am I an "I can do it" person? What am I holding onto that I could delegate if I spent 30 minutes setting someone up properly?
Is my bias on each project clear to me AND to my team—time, budget, scope, or quality?
Where am I hovering for updates because I wasn't clear upfront about when I wanted to check in?

Want to Try This?

Templates & Guides:
- Laila's* Delegation Template (the actual doc she uses)
- Nancy Fournier's* Delegation Assessment - A quick tool to help you pinpoint how well you're delegating and where you might be stuck
- Jesse Noonan's* 1:1 Template - pairs beautifully with delegation for ongoing coaching
- Skill/Will framework for determining level of involvement
Recommended Reads:
- Radical Candor by Kim Scott—Laila mentions this as foundational
- Article on giving positive feedback and why it matters (from Rare Bird): "Your job as a manager is to help your person go from intuition or happenstance to skill by locking it in."
Connections
- Reach out to Laila Plamondon* if you'd like support bringing delegation, project management, or communication trainings to your team. Email laila@rarebirdcoach.com with the subject line "Helia Help".
- Connect with Rare Bird for management training and facilitation support
- Work with Nancy Fournier* for leadership coaching to help you implement these practices. Email nancy@relishyourrole.com with the subject line "Helia Help".

*Helia Collective Member

About the Contributor

Laila Plamondon grew up in Bangladesh as the daughter of an American diplomat, studied psychology, briefly tried being a singer in New York, and eventually found her way to technology and education. She's now the Senior Director of IT at Uncommon Schools, where she leads a team of 20. But what lights her up most? Coaching and managing people, project management, and communication. That setter energy—figuring out who to set up next and how—is still at the heart of everything she does.

*Laila, #2, on the Volleyball team at the American International School in Dhaka*

This article comes from a coffee chat with Laila in October 2025. These conversations form the heart of the Helia Library – because I've learned the most from doing and from talking with other doers willing to share their wisdom. We don't need to start from blank pages or do everything alone.

As always, take what's helpful, leave what's not, and make it your own.

Love this article? Have a suggestion? We want to hear it all. Share feedback on this article here, and on The Helia Collective as a whole here.

Article & Resource Tags

Delegation That Actually Sets Your Team Up to Win

Build a GREAT Board: Nancy’s Relationship-First Framework

Mergers and Closures: Unexpected Ways to Move Your Mission Forward