Happy Friday, all!

This past summer, I found myself in a new chapter of my business journey: I’ve brought on a former colleague as a contractor and am transitioning her into a full‑time role at BTF. If you’d asked me a year ago whether I’d hire a full‑time employee here, I would’ve said, “Absolutely not.”

I managed people at my tax firm for a while, and it was challenging. At BTF, I’ve had contractors who didn’t quite work out. And frankly, the thought of taking responsibility for someone else’s livelihood felt intimidating.

Yet here we are. Why? Because she and I worked together for 7 years, I know she’s intelligent, diligent, and takes pride in her work, and that we already have a relationship built on open, honest communication. The thrill of what we might build together excites me. But there’s also anxiety: the weight of responsibility, the unknowns, the possibility that things won’t go as smoothly as I hope.

I know I’m not alone. I’ve had several conversations with clients this week who are feeling the same thing: the excitement of hiring someone new, paired with the stress of training, discovering each other’s working styles (and quirks), and being confronted with the fact that bringing someone on often holds up a mirror to our own leadership, our own growth edges.

If you’re managing or about to manage someone new, here are three core practices I’m leaning into—grounded in both my own experience and research on effective onboarding and management.

1) Set clear expectations from the start

One of the most critical responsibilities of a manager is to clarify roles, responsibilities, and mutual expectations. Research on onboarding shows that newcomers who have clarity about their tasks, their role on the team, and the organization’s culture are more likely to succeed and stay. Taking the time upfront—before or immediately when someone joins—to verbalize “here’s what success looks like,” “here’s how we communicate,” “here’s how I lead,” and “here’s how we’ll measure progress” helps avoid misalignment later.

2) Don’t shortcut the training process—actually hand over the work

It can be tempting when you hire someone you trust (and who you’ve worked with before) just to keep doing things the way you always did, rather than stepping into true delegation mode. But research shows that structured, ongoing onboarding (not just a quick orientation) improves productivity and retention. That means including on-the-job training: assign tasks to the new hire, provide feedback, then let them redo or refine them—rather than you silently doing them behind the scenes. Over time, you shift from “I’m training you” to “We’re building this together.” And yes: give yourself grace—there will be inefficiencies, mistakes, re‑work. That’s part of the process.

3) Keep open, honest, transparent dialogue—and generous grace

Bringing someone new into your mission-driven business means you’re not just hiring an employee—you’re inviting someone into your values, your vision, your way of working. That invites vulnerability: for them, for you. I’m feeling responsible not just for work output, but for someone’s livelihood. That’s real. And it means you have to talk about it. Share your hopes, your boundaries, your rhythms. Let your new hire ask questions and give feedback. Your strong onboarding process can build connections and reduce turnover. And when someone is learning—when they’re growing—give them grace. Mistakes will happen. This is the building phase.

As you coach or manage someone, or prepare to hire someone new, you might feel a mix of excitement and pressure. That’s normal. Instead of hiding the pressure, lean into it: it means you care. Use it as a signal to lead with authenticity and compassion.

Questions of the Week

1. What expectations have I clearly communicated to the person I’m hiring or managing—and what might still be ambiguous?
2. In what ways am I actively handing tasks to my new hire (not doing them myself), and how can I structure more opportunities for them to step in?
3. What conversation do I need to have this week (with my hire or with myself) around boundaries, vision, communication style, or feedback rhythm to build trust and transparency?

Tool of the Week

A simple shared “onboarding and check-in” template using a Google Sheet.

Why: Create a living document that outlines: role definition, key tasks for the first 30/60/90 days, training resources, who the new hire works with, and a recurring check-in schedule (weekly for the first month, bi-weekly for the next 2‑- 3 months). Use it together with the new hire—it becomes a co-owned roadmap.

How:

• Make a table with columns: Task/Deliverable | Who leads | By when | Status | Notes/Questions
• Add a tab for “Communication rhythms” (e.g., weekly 1:1, monthly feedback) and another tab for “Values & culture conversation” (how we talk, how we show up, how we handle mistakes).
• At each 1:1, update the document together: what did you complete? What questions do you have? What support do you need?

This tool helps anchor structure, makes the unseen visible, and fosters transparency.