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Melissa Shanahan

#160: Why We Call It a Quarterly Planning Retreat (and Why You Should Treat It That Way)

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What comes to mind when you think of the word “retreat?” You might think fancy spas and curating the perfect vibe for relaxing, and while this is true, it’s also the perfect space for evaluating and making smart plans for the future that you maybe don’t have the bandwidth to access on a day-to-day basis.

This week, Melissa is showing you why she calls her Quarterly and Annual Strategic Planning Retreats exactly that, and sets up her clients to treat these sessions as such. The turn of the quarter is your time to withdraw from the craziness that’s part of owning a business, having a family, and all the other obligations that make up your busy, full life, and you’ll hear why you’ll do yourself a huge favor by carving out time to retreat.

Tune in to discover the power of facilitating a retreat, and how to create a secluded space for you to get out of the surface-level stuff you’re doing in your everyday to focus on deeper, more powerful work for the future.

If you’re a law firm owner, Mastery Group is the way for you to work with me. This program consists of quarterly strategic planning facilitated with guidance and community every step of the way. The enrollment window for Mastery Group is open right now, so click here to join us!

Show Notes:

What You’ll Discover:

• What a retreat means.

• Why we call the quarterly strategic planning sessions that we host for our clients “retreats.”

• The power of intentionally retreating from your everyday life.

• Why Melissa recommends building in moments of retreat in between quarters.

• How to set yourself up for an effective intentional window of retreat.

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Create space, mindset, and concrete plans for growth. Start here: Velocity Work Monday Map.

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Digital Freedom Productions

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Full Episode Transcript:

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I'm Melissa Shanahan and this is the Velocity Work podcast, episode #160.

This podcast is for attorneys who are running their own firms. We explore tactics, tools, and stories related to pushing past simply lawyering well and into building a successful firm. Working in your firm and working on your business are two very different things. This podcast focuses on the latter.

Hey, everyone. Welcome to this week's episode. How are you?

I'm taking a deep breath because I'm at this crux right now, where we are rounding out the end of Q2. As I'm recording this, I have three more retreats that I'm very excited to facilitate before the end of the quarter. And then, we hit Q3. As you will be listening to this, it'll be July 5th, and that means we are officially in the last half of 2022.

The deep breath is just thinking about wow, in some respects, this year has flown by. And in others, I can think of certain points in the year, where it felt like it was crawling. Here we are. So, changes are coming. I'm going to fill you in on that.

We have an episode content, that we'll dig into today, that I think will be really good for each of you to think about. But let me fill you in on the changes. We are giving the Velocity Work podcast a facelift. You will see different cover art. We are changing the name of the podcast to be clearer for people who come across the podcast, to know who we're talking to. You'll hear a new intro, a new outro, etc.

The music is going to stay the same, because I love the music. I'm not really willing to give that up yet, so that is sticking around for the time being. And we're really excited about it.

We started working with a new podcast production agency in February, and we love them, over here. They have been fantastic to work with: Digital Freedom Productions. If anyone needs a good podcast production agency, Pavel is the owner. He's incredible, and so is his team.

When we first talked, Pavel said, “You know, I would highly recommend changing the name of your podcast Velocity Work. Nobody knows what that is or who you work with.” Was not the first time I've heard that advice by an expert. But every time I've heard it in the past, I wasn't really in a position to shift my attention and focus. To be able to give those resources needed to a really great rebrand.

Really, we were busy. We were growing fast. Things were working, and so it felt like it would be a distraction to pull away my attention and give it to the rebrand. We needed to focus on providing value to law firm owners, and we're still really focused on that.

But now, I have more capacity inside of the company where we can give a little bit of attention here, and keep everything going in terms of value, providing to law firm owners and our clients and members, etc. Then it hit me, the name of the podcast, and I thought, “Oh, that's too simple. There's no way that's available. That URL won't be available.” I was wrong. What I had in my head, was available.

So, I went to Digital Freedom Productions and said, “Hey, guys, what do you think about this title?” And they said, “Yup, think that that's perfect. Sounds great.” And we got to work on getting everything shifted in terms of the facelift, so to speak.

Next week, it'll be rolled out to you guys. You will hear it, and as a matter of fact, probably between now and then, there'll be a trailer that will come out so you'll get a little bit of a taste. But once the episodes really land, you'll hear it through and through; what the new podcast episodes will sound like, be like, what the cover art will look like, etc. Feels good. It feels like it matches us even more, which is a good sign.

Stay tuned for all that, coming your way very soon. Okay, today we're going to talk about the word “retreat.” And why, we here, at Velocity Work, call the quarterly strategic planning sessions that we host, why we call those “strategic planning retreats.”

The reason I'm doing a podcast on this is because I want you to think about, for yourself, how intentional you are with the space that you give to plan. So, we're going to talk about why it's called a retreat, and how we try to set our clients up to treat it as such.

I looked up the definition of retreat, and here's what I found, as it pertains to us and what we're talking about today: Time away in a quiet and secluded place. I also found the word retreat comes from the Latin root meaning “to draw back; to withdraw from the ‘real’ world; to withdraw from surface living and enter the deeper inner realms.” Okay.

Now, if “enter the deeper inner realms” is a little spiritual for you, let me say it a different way, just in case it will resonate harder this way: If you're taking planning seriously, it's important, when you sit down to plan thoughtfully, to be able to access the deepest answers you've got, to the questions that we are asking, during planning.

I have talked about what it means to make a good plan: You have to do a really great review of what you've just been through. You have to process lessons that you're going to carry forward, and really close that chapter well, so that you can begin the next chapter clean and purposeful.

So, having a space that is secluded, where you're withdrawing from the superficial life, so that you can access your own thinking, deep thinking, in order to make sure that you are closing intentionally one chapter and you're opening up another chapter.

Some of that is just what I said; processing lessons, etc., really thinking about accomplishments, taking stock of the quarter, or however long you're evaluating, and able to have vision for the future. Then, there's the nuts-and-bolts side of things, which also takes a lot of focus; it's a lot of math, it's a lot of numbers, it's getting the right numbers in front of you, it's calculating the right numbers that will help you give you the visibility that you want to have in the business.

To do all of this, you can't be in your superficial world with the phone ringing, and dings and pings, and people having access to you. You have to retreat from your everyday life. This is why we call, what we do for our members and for our clients, Strategic Planning Retreats.

We have quarterly strategic planning retreats, and we have annual strategic planning retreats. And they're all tied to a bigger vision, but it is a retreat. The visual that's in my mind for this, or just the way that I think about this for clients, members, and myself and my company, is that the turn of the quarter is your place to withdraw from the craziness that's a part of owning a business, and having a family and other obligations outside of work.

It's crazy, we all live busy lives; full lives. Taking a step back, it's like sinking into this deeper place to evaluate and to make great plans for the future. Smart plans for the future, that you don't have the bandwidth to be able to access those kinds of ideas, and that kind of evaluation day, to day, to day, to day, to day. So, this is your chance, every quarter.

And then, once the plan is determined, you know the steps because you did do the work of sinking in during that space of withdrawing, that retreat. Then, it's time to get to work. You get to work, and you live in that superficial space. I definitely recommend that you build in moments of retreat, or minutes of retreat, so that you're not just hustling the entire quarter; that's not what I'm saying.

But generally speaking, in terms of planning and the work, know that you take a retreat every quarter, and it's purposeful, and it serves your vision, and it serves your efforts, and it aligns you with where you really want to go. It's your opportunity to lift your head, because between quarters, your head should be down doing the work, honoring that plan that you put into place.

At the turn of the quarter, you lift your head, you take a deep breath, you evaluate, you look around, look to your right, look to your left in terms of what's behind you and what's coming up. You get settled and you make some decisions about what this quarter is going to look like, in terms of effort and the numbers that you're striving for, etc.

Then, you put your head back down, and you get to work on your plans. And then, you lift your head at the turn of the quarter as you sink into this retreat and evaluate, etc.

So, it's a really beautiful pattern. But the word “retreat” is important. Because if you just schedule a couple of hours or three hours to do your quarterly planning, something is falling short there. And if that's all you've got to give, you make the best that three hours. Take advice here, that I have, in terms of evaluation and looking forward.

But it is different when you say, “I'm going to retreat in order to really sink into this.” That's what we provide here at Velocity Work. And when I say provide, we provide the space, the physical space for private clients. They come on site, we have a conference room, it's outside of their four walls; they can sink into the space. I facilitate the thinking part of it all.

The groups that we lead, it’s a Mastery Group. For example, everybody comes on virtually, if they chose to attend virtually. Sometimes we have an in-person that they can come to. But they show up and that space is carved out for them. They know I'm going to be facilitating; asking the right questions, leading them through their workbooks so that they can come to their own answers, leading them through the math, the data, setting goals, determining ROCKS, all of that. They can count on me for that.

So, their job is to show up to this container, that we have provided, withdrawing from the superficial, typical life; the busyness, the pings, the dings, the distractions, the interruptions, the client work, all of that. Their job is to retreat from that and drop into the space.

The word “retreat” really is appropriate. We have a private client who's hilarious, and he always gives me a hard time about the name “retreat.” He thinks we should name it something different than “retreat,” because he's associating the word “retreat” with; a sanctuary, a spa, and relaxing, kick your feet up for, you know all of that. And it's work.

When you come to this container, when you come to this space, you really have to think deeply about things. But it is the space to do so, and it is the way to get out of all the work that lives on the surface, that you're really digging into, typically, day-to-day. It's a way to take a step back from that and allow yourself to sink in.

So, I am not changing the word of our retreats; it’s going to remain retreat. That's we're going to call it. This is why: I thought it would be a fun podcast to do, because in case any of you wonder, “Why is it called a retreat? Okay, it's a virtual meeting, Melissa.”

Yes, but it's a container. And you treating it as a retreat for yourself; to plan, and to be thoughtful and reflective, and access your own answers that you need in order to make the best plans moving forward... You thinking about it like a retreat, and setting it up that way for yourself, when you come to the container we provide, makes all the difference.

I can tell the people who come to, even the virtual ones for example, and they're checking their phone, you can see that they're doing something else on the side, and you know, they get to do whatever they want to do. And, sometimes there is an emergency, but not very often. Very often it's because we didn't set expectations with those around us. We didn't make sure that we carved out the space so that we can sink into this work, and so therefore, you're having to deal with the little things, the little poles that you have, in those moments.

Treating it like a retreat, you will get more out of yourself in that time. It'll be deeper work, more focused work, you'll have better plans. It's just better. So, that's why we call it a retreat.

Now, if you aren't a client of ours, then there's still a way that you can set this up for yourself. I think we do a fantastic job of providing the container for you in the workbook, and facilitating the questions. You don't have to think about any that. The cognitive load is eliminated for you when you sign up for Mastery Group, for example.

However, if you want to do this on your own, you should know ahead of time exactly what you're going to accomplish in the window of time that you set aside for yourself, to retreat from the world. Have specific questions lined up that you're going to answer. Have specific things that you want to have accomplished in that time.

So, setting goals, for example, determining what numbers you are shooting for. That's what I mean by setting goals. And then, deciding what priorities need to happen, in order to hit those goals. Coming out of your retreat with those answers, you'll set yourself up to win at that game.

When it's facilitated, we do that for you. It's not impossible without us, but you do have to give some forethought to all of this; to make sure that when you drop in, you know what to do, you know what to ask of yourself. That will allow you to sink into the questions, so that you come out with the answers that make the most sense for you, and for your firm.

I've done this before. We've all probably done this before, where we sit down into a window of time, and it just says something vague, like business planning retreat. Okay, what am I supposed to do? How should I think about this? All of a sudden, you have to make a bunch of decisions before you can even sink into the work. So, deciding all of that upfront, so that you can drop in, is really important.

This is the same with your calendar, right? Like, you’ve got to put exactly what you're supposed to do on the calendar, or else you have to find your groove to figure out what you're supposed to be doing. You know that the subject matter you're going to be dealing with, but you don't know exactly what you're going to do; that was calendared poorly. That did not set you up to win, at that space of time.

It's the same thing for a retreat; calendar it well, and know what you're going to do exactly, in that space, and you will come up with a really great plan for your next quarter, for example. So, you can do this on your own.

A couple other things I'll say is, you can decide what is the environment that you're going to put yourself in. I highly recommend getting out of your four walls. If you can put yourself into a space that feels, there's an energy to a space, what energy and what space do you want to walk into? Is it a hotel, that's nice, that's local? Is it a retreat into the mountains, or rural? Is it renting a conference room somewhere, that's really beautiful and inspiring?

And if you can't, for whatever reason, get outside of your four walls, and you're going to do it in the comfort of your own home, or at your office, just make sure to set yourself up so it feels like a retreat. So that it feels different than just a workday.

You can light a candle. You can get a cup of tea. Have a bit of ritual around how you sit down and curate the vibe of the space that you're going to be in, even if it is your office or your home. I would say do that, no matter where you are; hotel, really cool conference room, or out in a cabin in the woods, no matter what you do, or in your home or your office. Curate the environment. Be really thoughtful about that.

Another thing I would say is, make all your decisions ahead of time. Make sure that you're not having to decide what's for lunch, where you're going to go, none of that. The only mental task that you have that day, is to have access to the right questions and your own answers. And your willingness to focus and sink into this work. That's what will matter.

So, if you can just have snacks on hand, so that you're not having to worry about any of that; have coffee, have the tea, have water, have all of the things around you that you might need, so that you can sink into the work and you don't have to start making decisions in order to suit yourself.

Get creative about how you curate your environment. If it's virtual, maybe you have some accountability partners that you want to do some quarterly planning.

It's like, “Okay, we're going to show up together on this call. These are the questions we're going to ask ourselves. These are the numbers that we're going to decide on. These are the ROCKS we're going to decide on. So, we're going to break up the day into three sections. Let's meet and kick off together, and then keep our cameras on but mute ourselves and get to work. And then, at this time, we're going to come back on and say what we got accomplished. Then, we're going to do it again.”

So, it's almost like having work sessions with friends. Now, I'm just spitballing ideas, but really, you will do yourself a favor by thinking about planning for your business, and the space that you do that in, as a retreat, for every angle.

There are probably things, that I haven't mentioned here, that your brain is having ideas on how to make it feel more like a retreat. That allows you to focus. Expect that of yourself. Expect that you're going to think deeply. Expect that you're going to ask hard questions, and that you're going to come up with numbers. Not kind of what you're shooting for; specifically, what you're shooting for. Expect that you're going to identify key priorities that are going to make a difference, they're going to have a great impact inside of the firm.

All of this can happen so much easier, if you give yourself the space. If you retreat. If you withdraw from the surface, day-to-day work and life. For a short amount of time, pullback; curate your environment beforehand, make those decisions about how your environment’s going to be curated, and make decisions about what you're going to need that day ahead of time, so you have everything you need. And then, allow yourself to be with the work.

Alright everybody, I hope this is helpful. Come with us. You can take part in our retreats, the Mastery Group. You can go to and learn about how to get on the waitlist. Or, if you're listening to this during an open enrollment period, you will see a way to enroll. We'd be happy to facilitate this for you. But even if we don't; do it for yourself.

Alright everybody, have a beautiful week. I'll see you here next Tuesday.

Hey, you may not know this, but there's a free guide for a process that I teach called, Monday Map / Friday Wrap. If you go to, it's all yours. It's about how to plan your time and honor your plans, so that week over week, more work that moves the needle is getting done in less time. Go to to get your free copy.

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