Overcoming the planning fallacy with predictable legal billing

Only 30% of people can accurately predict how long a task will take them.

Pretty wild, right?
Especially for all of us consultants, lawyers, and anyone trying to promise predictable billing?!

It's called the "planning fallacy," and it's why we constantly feel like we're running out of time or why our to-do lists are overflowing.

If you're nodding along, here are some tips to keep from derailing your day:

-Add 30% to your time estimate. Think the task will take an hour? Make it 90 minutes. Future you will thank you.

-Ask someone else. Apparently, we're better at estimating how long other people's tasks will take. So, grab a co-worker and ask for their take; they're probably less optimistic about your superhero timeline. Don't have a co-worker? (We have a service offering for that. WINK, WINK.)

-Break it down. Big projects = overwhelming. Break them into smaller tasks, estimate the time for each, and watch how manageable it all feels.

-Check your receipts. Look at similar projects you've done before. If that pitch deck always takes two weeks, stop kidding yourself that this one will take five days. (Spoiler alert: it won't.)

-Sleep on it. Revisit your timeline tomorrow; I know, I know. My impatience dies at writing this, but a fresh set of eyes (and a rested brain) can help spot unrealistic goals.

Good time management isn't about squeezing in more.
It's about setting yourself up to deliver on time without the sweaty stress spiral.

How to answer: What makes you different as a lawyer?

“What makes you different?”

It’s a question we used to ask lawyers all the time.
Here's the problem with that. It’s all about you.

And when lawyers are trying to connect with clients, “you” isn’t the point.

While some clients might care about what makes you different, they really care about how you can help them.

So, we reframe in our 1:1 lawyer coaching sessions.

Instead of asking, “What makes me stand out?” ask:
- What do I have that will make my client’s life easier?
- What will help them solve problems, avoid risks, or get closer to their goals?
- How can I make it easier for my clients?
- What do my clients need from me?
- How can I show up in a way that makes their job easier, their business stronger, or their life better?
- How might I help?

When I work with lawyers, we focus on exactly that.
That’s the differentiator.

The answers are almost always right there if you’re paying attention.

Sample Script for Virtual Meet + Greets

You have a new contact who has agreed to a virtual meet and greet!

Now, what do you talk about? We hear this all the time in our 1:1 lawyer coaching sessions.

Start by warming them up, especially if this is a brand-new "cold" relationship.

While we typically go into meet and greets without a formal agenda, do some sleuthing before the chat.

Find out where they live, what they do, how you might be able to help them (and notice that I did NOT say SELL to them), and what they have posted about recently.

The purpose of the meet and greet is to get to know each other. Often, we say this upfront so they know that this call is not a sales pitch.
Plus, you never know where the call might take you!

SAMPLE SCRIPT [If you say you are excited to meet, then act excited!!]

Hey!
Thanks so much for agreeing to jump on and chat with me. I have no formal agenda today other than to get to know you. Why don't you go first and tell me about you? What's new?

Why 1:1 lawyer coaching is for you

If you struggle with what to say on a meet and greet…
If you struggle with how to network…
If you struggle with making time for business development…
If you struggle with following up or knowing how to respond…
If you struggle with the next steps after conferences…
If you struggle with visibility within your firm...
If you struggle with origination…
If you struggle with building relationships…
If you struggle with what to post…

Let’s chat!

Business development activities when you hate business development

Hate business development? We hear this all the time from our lawyers during our coaching sessions.

Try connection-building activities instead:

- Set up regular check-in calls with your current base of clients.
- Organize informal idea exchange sessions instead of just catch-ups and ask for their perspective.
- Check in with former colleagues without any agenda. Simply check in and see how they’re doing.
- Shift your mindset. Think about how you can help solve problems, be curious, and ask questions. This takes the pressure off of you!
- Write a quick note to a warm contact. Keep it simple, and send a coffee gift card if you’re feeling generous.
- Sign up for pro bono work. You’ll meet people who care about the same things you do, and the connections happen naturally.
- Collaborate on something small with a client or prospect.

Selling yourself as a lawyer

“I don’t know how to sell myself.” - Does this sound familiar? We hear this all the time from our lawyers.

You don’t have to sell yourself in every meeting!

In fact, focusing on selling only could shift your thinking into showing up in a completely inauthentic way.

Instead, approach each meeting by asking yourself and the person you are meeting with: “How can I help and support you”?

Additional questions to consider asking:
What’s top of mind for you?
What are you struggling with?
Would X be helpful?
Who else could I introduce to you?

Then listen.

Build the relationship and give yourself permission to get back to them with potential solutions.

This approach can be used in meet and greets and with existing clients.

It takes the pressure off to sell and pitch.
It removes the urgency of thinking, “I only have one shot at this opportunity.”

Focus on how you can help.

Your door opener

As a lawyer, if are going to give away something for free that you ultimately want people to pay for, it's gotta be good.

You have to make the offer, checklist, second review, etc, so good they can't imagine their life or business without it.
-Show the value.
-Show people what it's like to work with you.
-Identify things they might not have thought of.
-Hook them.

This isn't about aggressively chasing them with free samples or adding a throwaway like floormats.

Instead, aim to"offer something genuinely valuable (like 4 free business development coaching sessions, for example).

Create an offer that is so valuable that they all become clients.
Create an offer so good that they become your ambassadors without being asked.

Does your offer do that? If it doesn't, let's chat.

So Much To Say:A Legal Podcast For People

Come and explore the behind-the-scenes of work, life, and everything in between. We’re your hosts - Megan Senese and Jen Ramsey.

And we’re here to showcase the human side of the legal world, from marketing and consulting to the very real struggles of balancing work with being human.

This isn’t your typical, dry legal show. We’re bringing you real stories, candid conversations, and smart insights that remind you that outside of being a lawyer or legal marketer - what makes you human?

So whether you’re navigating billable hours or breaking glass ceilings in a woman-owned practice, this podcast is for you.

Stay human.

Stay inspired.

Namaste (or whatever keeps you human)

Listen here

You’re a New Law Firm Partner. Now What? 5 Tips for Your First 90 Days

Congratulations! You just made (read earned) law firm partner. It’s a monumental achievement that deserves a moment of celebration.

While you’re basking in this glory, you might also be thinking, “What now?” You’re not alone if you’re feeling a mix of excitement and a pinch of panic. Many new law firm partners stare blankly at their desks, wondering how to capitalize on this opportunity or which steps to take first. There might even be some fear and wondering if your overwhelming feeling is normal. It is.

Or maybe for you, this is the moment you have been waiting for, and you are ready to wield all the power that you have longed for. Not so fast. It takes some adjustment for the firm to catch up to you being an “owner.” You also might need to adapt to a new owner’s mindset with intentionality about where you spend your time. Others will now look to you as a leader, and your behavior needs to reflect that.

Your approach over the next ninety days will set you up for a strong year. You need a strategy to guide you. These five tips will help prove to key stakeholders who voted you in that you deserve to be law firm partner and they made the right choice to promote you.

Build Authentic Connections (Days 1-30)

If you have not built connections before reaching your partnership status, now is the time. Think through how you will invest your time and resources to develop genuine connections and relationships. Approach each interaction with intentionality, kindness, and curiosity. Contacting people only to win work is off-putting. Your first month is all about building genuine relationships that go beyond surface-level chit-chat. Ensure you have a healthy mix of external and internal networking.

For external networking, schedule coffee dates or lunches and treat these encounters like mini-networking power sessions. Be genuinely curious; people love to share their stories. Ask questions that dig deeper:

• What’s the most exciting or difficult project you’re working on right now? This questioning ensures that you spend more time talking about the client and less time focusing on yourself.

• How can I support you? You might not have the solution right away but the more people you meet with, the more connection you will be able to make later down the road.

Network internally with colleagues—across the firm, in different geographies and in different practice areas—as they can position you for success. Connect with other newly minted partners and explore ways to collaborate with each other. Set up meetings with established partners and let them know you are still available for new matters and incoming assignments as these will still “feed” you as you develop your own book. Apply the same curious mindset with internal networking and ask questions:

• For partners: What is one thing you wished you knew before you became partner?

  For marketing and business development professionals: What initiatives do you recommend I get involved with? What pitch opportunities are upcoming?

  Show Gratitude (Days 31-60)

As you move into your second month, spread gratitude. Your journey to partnership didn’t happen in a vacuum; there were plenty of people who helped you get there. Send them handwritten thank you notes. Be as broad as possible as you spread gratitude around. This is also an easy and subtle way to inform people that you made partner without being boastful.

Many of us seek “excuses” to contact our clients, contacts, and prospects. This is one of those excuses. Organize and host a gratitude party to thank your mentors, clients, and internal stakeholders who supported you as you climbed the ranks. This is not just any gathering—it’s a celebration of relationships and appreciation, a chance to solidify connections, boost morale, and set the tone for future collaborations. Consider these tips for your gratitude event:

• Craft Personal Invitations: A handwritten note or a personalized email goes a long way. Make it heartfelt—tell them how much their support means to you.

• Share Your Vision: During the event, express your gratitude and share your vision for the future. Talk about how you plan to keep delivering value and support to their businesses.

• Connect Others: Use the event as an opportunity to give back. Expand your network and reach by connecting similarly situated clients who could develop mutually beneficial relationships.

  Get Savvy About Your Finances (Days 31-60)

The new compensation is one of the most often overlooked areas with the new partnership role. Yes, the consensus is that earning partner will get you more money. Before you run out and make a large purchase that you might regret, find out as much information about HOW your new compensation works. Understanding where your incentives are will help define what type of work is the most beneficial to the firm and to your practice group.

Determine if your firm has a black-box pay model. Do you know how your firm handles required capital contributions, origination credit nuances, and credit splits; what is their policy on collections or billings; and now that you are a partner, how is health insurance handled?

Begin having conversations with trusted people within the firm. Ask them what to look for and what lessons they learned. Schedule a meeting with your financial advisor or the firm’s finance team to get the lowdown on your compensation structure.

Arming yourself with this financial knowledge empowers you to set realistic expectations and make informed decisions that not only impact your pocket but your business development strategy as well.

Tap into Internal Resources (Days 61-90)

Now that you’re getting your footing, leverage your internal resources. Collaborate with your marketing and business development team to learn how they can support your goals. They can work with you to add you to the appropriate teams for pitches, speaking opportunities and initiatives. Tap into the team by asking questions:

• How can I support the firm’s initiatives? What affinity groups should I join?

• What internal practice/client team/industry group would support my book? Are there upcoming practice group meetings that I could present at?

• What client development initiatives can I dive into to connect with potential clients? Can you help me devise an actionable plan that I can stick to?

• How can you help me organize events that lean into my strengths?

• How can I organize and prioritize my network of contacts and develop a robust pipeline of clients, prospects and referral sources?

• Which publications or news outlets would be best suited for my skills?

These internal resources can provide the tools you need to build a marketing plan that showcases your unique strengths.

Additionally, familiarize yourself with the firm’s support structure, including practice group leaders and administrative professionals. Engaging these resources will foster collaboration and make it easier for you to excel in your new role.

Set Bold, Achievable Goals (Days 61-90)

As you settle in, map out a path forward. Small business development steps each day will compound over time. Setting bold yet realistic goals is essential to your success. Identify areas where you want to grow for attracting new clients, strengthening existing relationships, or collaborating on high-profile projects.

Here’s how to make your goals SMART (Specific, Measurable, Achievable, Relevant, Time-bound), for example, a newly minted healthcare partner:

• Specific: “I will target hospitals, physician groups, and startups in digital health to increase awareness of my practice in healthcare compliance and regulatory guidance.”

• Measurable: “I will reach out to three new contacts in these healthcare sectors, and I will attend two healthcare related industry conferences this quarter.”

• Achievable: “I will leverage the firm’s marketing team for support and collaborate with senior partners for introductions to key industry players.”

• Relevant: “I will build a strong personal brand and client base that aligns with the firm’s emphasis on partner-driven business development.”

• Time-bound: “I’ll hit this milestone by the end of Q1.”

Celebrating your achievements will boost your confidence and keep you motivated. Whether you like it or not, you are in a sales business—and sales requires building relationships and resilience.

Transitioning into a partnership is a thrilling journey packed with new opportunities and challenges. By building authentic connections, expressing gratitude, understanding your financial landscape, leveraging internal resources, and setting ambitious goals, you’ll lay a strong foundation for success in your new role.

This is your moment to shine—for yourself, the firm, and your clients. Arm yourself with these strategies and embrace this new chapter with enthusiasm and confidence.

This article is published on PLI PLUS, the online research database of PLI. The entirety of the PLI Press print collection is available on PLI PLUS—including PLI’s authoritative treatises, answer books, course handbooks and transcripts from our original and highly acclaimed CLE programs.