The One-On-One: Ensuring the Success of Your New Leaders: A Manager's Guide, Part 2

In my previous post we discussed the importance prioritizing our new leaders, being mindful about their onboarding and training, and tools to provide them support. This is a multi-part series because in the realm of leadership, one of the most crucial responsibilities for senior leaders is setting your team up for success, both individually and collectively. Today we'll look at the importance of one-on-one meetings and I'll share some tips for a great meeting format.

Too often I’ve watched good leaders leave and then listened to their supervisor or senior leadership talk about how it was the employee’s choice, they weren’t the right fit, they found a different opportunity, they were never really bought in, etc. The supervisor’s commentary is all about the employee. Rarely do I hear a senior leader reflect on the turnover of an employee and look at their own responsibility.

When employees fail or leave, it's imperative to acknowledge and address the role we, as a supervisor, may have played in their struggles. While some individuals may not be the right fit for a particular position, there are always opportunities for improvement in terms of supporting and guiding our team members. How often do we, as senior leaders, critically evaluate our role in the turnover of our staff? One of the areas we need to examine is how much we were actively, effectively and regularly communicating with them. One method to address this regular communication is by having a regularly scheduled one-on-one meting.

Effective one-on-one meetings are a cornerstone of successful leadership. These meetings provide a dedicated space for open communication, fostering trust and rapport between you and your employees. Hopefully you’re meeting individually with your direct reports at least every 2 weeks, maybe more often in the beginning. If this isn’t a regular practice, I highly encourage you to add it to your calendar. Let's look at setting up a successful one-on-one.

Prioritize the meeting!

How much you prioritize your team members sends them a loud message about how much you value them. So, if you’ve got a set meeting date with your folks – and this includes one-on-ones as well as team meetings – make those meetings! They block out the time and make sure nothing else gets in the way. When you don’t respect that enough to do the same it says to them that they aren’t important, which can lead to frustration and dissatisfaction.

Yes, emergencies do come up, but every time we reschedule (aka cancel) we chip away at how much they feel like they matter. When we cancel, we are choosing something else over our employees, so I encourage you to choose carefully what you opt for instead of them.

It might seem strange to have a format or agenda for a less formal one-on-one with your employee, but for a new leader it can really help remove some of the stress by helping them know what to expect and how to prepare. It also helps ensure the time you've set aside actually results in sharing important information and building relationship. I’ll show you my suggested format here and then get into the why & how.

One-On-One Agenda

1. Initial greeting

2. Operational Agenda Items

3. Hard Things, Roadblocks, Mistakes & Misses

4. Celebrations

5. Anything else

6. Items for Follow Up

7. Gratitude

Let’s break down the details…

Greeting

Our body language says so much more than our words, so be thoughtful about how you welcome them. If the meeting is in your office, as soon as they arrive stop what you’re doing, SMILE, say hello, turn to face them, make eye contact and give them your full attention. If you’re in the middle of an email, and will forget what you’re going to say if you don’t finish it (been there) let them know you’re just finishing an email but to please have a seat. Next time, wait to start that email until after your meeting so you can immediately give them your attention upon arrival. If you’re meeting somewhere other than your office (see the bonus tip about location below), make sure to be on time, or a little early, and to be ready to go.

Focus on them, not you. Ask how they are doing rather than sharing how busy you are or how crazy your day is. If your new leader has shared something personal with you (new puppy, upcoming vacation, family news, child accomplishment, etc.) this is a great time to ask about that. It shows you’re paying attention, that you value them as a human and helps build a relationship.

Operational Agenda Items

These are things going on in the work setting that need to be discussed. This could be events coming up, collaboration updates, staffing issues, program updates, budget conversations, facility needs, etc. It’s important to have a system in place for how to build the list of these operational agenda items for each meeting. Some options include:

• You both email each other your list 24-48 hours before each meeting. (This method is my favorite because it helps you both know if you need to prepare any info.)

• You both write your list on the dry erase board in the meeting room when you arrive

• You both share your list with each other when you get to this point in the meeting before jumping into to the items themselves.

These lists should be headings, save the details for the conversation. Set up a system that will work for the two of you and then stick to it so your new leader feels more comfortable knowing what to expect and how best to prepare.

Hard Things, Roadblocks, Mistakes & Misses

Myself and many of my share the mantra “We Can Do Hard Things”. I train on it and we talk about it, so I really like the phrasing here but you can use whatever language works for you. The important piece is specifically setting aside time to talk about the challenges, and being intentional about the questions you ask. An added bonus is that listing it as an agenda item helps normalize hard things.

Especially in the beginning, they may not have a lot to share here. Perhaps they haven’t stumbled across any really hard things yet, or maybe they have but aren’t sure it’s safe to share them with you. That’s OK. It may take a number of meetings before there is anything they want to share in this section but please keep this on your agenda and hold this space. There will come a time when they do have something to share and this can be one of the most important moments in your relationship with them. Create space for the conversation and if they don’t have anything initially, allow some silence before moving on to the next item.

Bonus tip! Get comfortable sitting in silence. It can be uncomfortable for some folks and I’ll often tell them that I’m going to purposefully give us a few minutes of silence so we can really think about the question and have time to respond. The trick is to not let our own discomfort cause us to break that silence. The more you practice, the more comfortable it becomes.

When you get to this part of the agenda, be thoughtful about the questions you ask. If you ask things like “How’s it going”, “Is there anything I can help with” or even “Are you having any challenges”, it's easy for them to say everything is fine. Trust is earned. You have to show them that it is truly OK to ask for help and that you won’t be disappointed when they make a mistake. So, ask one or two questions that assume there have been challenges (which normalizes them) and are designed to invite the details, like these:

• What’s been the hardest thing you’ve had to deal with since we last met?

• What’s the one thing you went home and vented to your friend/family/significant other/pet lizard about in the last 2 weeks?

• What was your least favorite work day since we last met & why?

• Tell me about the mistakes you made since we last met?

And then - and this is likely the most important part - be extremely mindful of your response when they do tell you something. Lean into how they must be feeling and acknowledge it. Validate their feelings:

• Wow, that must have been hard.

• That sounds like it was very frustrating.

• I’m so sorry you had to deal with that.

When I say “lean in” I mean to really hear, and believe, them. Please don’t try to talk them out of their feelings, or tell them that what happened “isn’t a big deal” or that they shouldn’t be so upset or concerned. Viewing a situation through the eyes of a seasoned professional rather than a new leader is a very different perspective and those sorts of comments only make them feel worse. Just listen and acknowledge what they tell you. A great follow up, especially if they don’t say a lot, is to say “please tell me more”. This is one of my favorite phrases. It allows me to pause and process my response, while also giving them the opportunity to give me more information.

The next step is to ask what they need. Sometimes just sharing the situation with you is enough. First, and importantly, thank them for sharing this with you. Next, ask how you can support. That can sound like this:

“Thanks so much for sharing that with me, it helps me support you by knowing about struggles you’re having. How can I support you with this? Would you like my input on how you handled it, or is it enough to have just shared it with me?”

Then pause to allow them to think about that and abide by their response. As seasoned leaders, it’s often easy for us to have an idea of a different way to handle a situation, but they don’t necessarily want to hear it. So, ask them if they want feedback before offering it.

Bonus tip! If they do want feedback, let them know you’ll definitely give them some input but first invite them to share with you ideas they have as to how they might handle the situation differently if it were to arise again. We are able to come up with ideas quickly because we’ve had lots of experience to learn from. They’ve just had one of their first learning opportunities. We can best help them develop important skills like analyzing situations and learning from them by inviting them to debrief it with you. Say something like

“Before I share some ideas, what are some thoughts you’ve had about how you might handle it differently if a similar situation occurred again?”.

Their response is a great opportunity for you to help bolster their self-confidence. As they are sharing, give them positive feedback on good ideas they mention.

Lastly, before sharing your ideas, reinforce the good things they did. This can sound something like

“I really appreciate the opportunity to talk through this with you. I know this was a tough situation and I think you did a really good job handling something that was completely new to you. I like how you ____________ and I think your idea of doing __________ next time is really good. Other thoughts that came to mind for me if I had to handle a situation like this would be to _______________.”

Celebrations

It’s important to not just dwell on the tasks and the hard stuff! Make sure to take some time to celebrate the wins, big or small. Again, be thoughtful about the questions you ask. Here are some suggestions:

• Tell me about a moment that made you smile since we last met?

• What was your favorite thing you accomplished since we last met?

• Tell me about someone on your team who you’re impressed with or proud of and why.

• Is there anything going on outside of work that you’re proud of or excited about that you’d like to share?

Another great one, especially if they have been reluctant to share the hard things is to ask “Tell me about a time since we last met when you figured something out, or learned something, that you didn’t know before?”

It might feel strange to think about scripting out questions, but consider how we prepare for an interview. We are thoughtful about the kinds of questions we ask. Why would we give that much care to someone we haven’t even hired and then not give that same care to someone on our team? How we ask questions is an important tool in getting the information we are really trying to get. I promise you that taking the time to think about how you want to ask questions will pay off in the long run. And one other tip on this - it’s absolutely OK to write down the questions in advance. It just shows you took the time to prepare, which again sends the message you value your new leader and your time together.

Anything else

Make sure to provide them the opportunity to share anything else they were hoping they’d be able to discuss with you.

Items for Follow Up

Throughout your time together you may have come up with tasks or follow up that either of you are going to be responsible for and you took note of that throughout. You’ve covered a lot in this meeting, so make sure to re-cap what those follow up items are, clarified who is responsible for what, and assigned a deadline to have the tasks done. Make sure you both agree that the list is complete and let your employee know you’ll send an email as well so you’ll both have the list to work from.

Gratitude

As you wrap up the meeting, thank them for everything they’ve done and for sharing with you (ideally name 1 or 2 specifics to show you were paying attention). Tell them how grateful you are for their hard work, or that they are on your team, or whatever feels right for you.

Post-meeting

Make sure that when you schedule this meeting on your calendar you include an additional 15 minutes to complete these important post-meeting tasks. We forget details quickly, especially once we jump into our other responsibilities, so it’s important to do this immediately after the meeting. As soon as they leave take some time to debrief this meeting yourself and make some notes for yourself on these and other thoughts you may have:

• What did you learn about this employee?

• If they shared challenges, how did you feel about how they handled them and their ideas of how they’d handle them in the future?

• Did anything they share with you indicate any areas in which they may need additional training? If so, what’s your plan to secure that for them?

Writing down these thoughts after a meeting help get them to stick in your brain and provide you a valuable tool to use in future conversations with them and plans for their development.

Next, take a few minutes to send them that follow up email you mentioned. This helps document the meeting for both of you and is a great opportunity to reinforce the gratitude you shared with them. Make sure to include the follow-up items, who is responsible for each, and the deadline they items are to be completed by. Make sure to note yours in your calendar or task lists so you remember to complete them on time as well. We build credibility and trust by following up on things we’ve committed to for our team.

By sticking to a format, you’ll continue to build that trust and let your leaders know what to expect. While they may not have a lot to share in the beginning, that should change over time as they get more comfortable with you and with the meeting style. On that note, know that your first meetings may be relatively short but they may get longer over time, so plan accordingly.

Bonus Tip! Location, location, location! Think about “home field advantage”. Your office holds power and increases the intimidation factor. It’s likely your new leader will feel more comfortable meeting in their office or in a neutral conference room or other private space. If you do need to meet in your office, come out from behind your desk. If you’ve got a table in your office, that’s a great option. Otherwise, set up your chairs across from each other on the front side of your desk. This can create a more open feeling that can increase the comfort level for your new leader.

I hope you'll implement some of the suggestions here and that you'll find them helpful. I'd love to hear how it's going, so feel free to comment here or send me an email. Now head on over to the third and final post in this series where we'll talk about ongoing support and keys to increasing the satisfaction and retention of your team.