September always feels like a turning point. Summer distractions fade, people settle back into routines and work picks up again. It’s easier to get someone on the phone, to schedule a coffee or to restart a conversation that slowed down over the summer. In many ways, this is the best season for business development because your outreach is more likely to get noticed.

That shift makes fall one of the best times to focus on business development. A thoughtful note or a coffee invite can stand out in a way it might not during other parts of the year. By using this season to reach out you can build momentum that carries into the new year.

Business development often feels like a big task, but small consistent steps move the needle. When you focus on a handful of actions you’ll keep yourself visible and connected without feeling overwhelmed.

Start With Five People

A lot of people get stuck on business development because they picture an endless list of names and convince themselves they’ll never get to everyone. The truth is you don’t have to. The best way to start is small and focused. Choose five people who actually matter to your growth and put your energy there.

Think about:

  • Referral sources who’ve sent you work in the past.
  • Former clients who had a good experience with you.
  • Potential clients who know your name but haven’t hired you yet.
  • Industry contacts who influence conversations in your space.

Focus on people who already have a connection to you. That’s where you’ll see the best results. Think about a client who recently moved into a new role and now has different responsibilities, a colleague you met at a conference who works in an adjacent field or someone who commented on your LinkedIn post and showed interest in your perspective.

Reaching out to five contacts like this each month is manageable and realistic. Over the course of a year, that becomes 60 genuine touchpoints. Each of those touchpoints is a chance to strengthen a relationship, learn what someone’s focused on and remind them of the value you bring. That’s how opportunities build — not from one-off efforts, but from steady, thoughtful contact that compounds over time.

Do Your Homework

One of the easiest ways to get ignored is to send a note that feels like it could have gone to anyone. Busy professionals spot generic outreach right away, and it often ends up deleted. What stands out is a message that reflects something real about the other person, something that shows you noticed what’s happening in their world. That requires a little preparation, but it doesn’t take long.

Here are places to look before you reach out:

  • LinkedIn updates: Promotions, new roles and work anniversaries are easy conversation starters. Articles or posts they’ve shared show you what’s on their radar. Comments they’ve left on other posts give you insight into where they’re spending attention.
  • Company websites and press releases: Firms and businesses regularly announce office openings, major deals, new hires or new practice launches. These updates give you an immediate reason to reach out and position you as someone who’s following their progress.
  • Industry coverage: Trade publications and news outlets often feature professionals in your network. If someone was quoted in a piece, spoke on a panel or received an award, referencing it shows you’re paying attention to their expertise and visibility.
  • Social activity: Beyond LinkedIn, many professionals post on other platforms or engage with industry groups. A like, share or brief comment can reveal what they’re thinking about and give you a natural entry point for your outreach.

Once you’ve gathered context, bring it into your message. A quick reference is all it takes:

  • Article: If they wrote or shared something, call out a specific point that resonated and ask a question to continue the conversation.
  • New role: A congratulations note that also asks what they’re most excited about in the position is more personal than a generic “Congrats.”
  • Firm or company news: Point to a new practice or initiative and ask how it will affect the clients they work with. It shows curiosity about their world, not just your own agenda.

I hear from many lawyers that they don’t know what to say in outreach. The truth is, the material is almost always right in front of you. Spending even a few minutes on LinkedIn or the firm’s website gives you plenty to work with. The difference between a forgettable “just checking in” message and a meaningful conversation often comes down to whether you did that little bit of homework.

Keep It Personal

Most people can spot a generic email or LinkedIn message right away, and they usually delete it without reading. Mass outreach rarely works because it feels like no effort went into it. The messages that get answered are the ones that feel like they were written for one person, not a mailing list.

Think about what would make you stop and read a message in your inbox. It’s usually something specific — a note about a recent article you published, a mention of an award you received or a thoughtful comment about something you posted online. It doesn’t take paragraphs of writing. One or two lines that show you were paying attention is often enough.

The key is to make the other person feel seen. If a client just got promoted, congratulate them and ask what they’re most excited about in their new role. If someone in your network shared an article, let them know what stood out to you and why. If their firm announced a new initiative, ask how it connects to the work they’re doing. These little touches shift your outreach from transactional to relational.

Here are a few examples:

  • “I saw your article on ESG trends and thought your point about investor pressure was spot on. How’s your team handling this in practice?”
  • “Congrats on your new role at XYZ. Would you be up for a coffee sometime soon to catch up?”
  • “I noticed your firm launched a new practice. I’d like to hear more about it and what it means for your clients.”

Remember, the point isn’t to pitch or sell in the first message. The point is to start a real conversation that can grow over time. Personal touches open doors that mass messages never will.

Invite a Conversation

After you connect with someone, don’t jump straight into talking about yourself. Suggest an easy next step that feels natural — a coffee, a quick call or sending along something useful. The point is to keep it light so the other person feels comfortable saying yes.

Most people don’t want a pitch. They want a real exchange. When you ask about their work and listen to what matters to them, you start a conversation that can grow over time.

Here are 10 prompts that feel natural and not forced:

  1. “Want to grab coffee and catch up?”
  2. “Let’s connect soon — I’d like to hear how things are going.”
  3. “If you’ll be at [event], let’s plan to meet.”
  4. “I’d like to hear your thoughts on [topic].”
  5. “It’s been too long since we spoke — want to fix that?”
  6. “I saw your update on LinkedIn. Can we set a time to talk more about it?”
  7. “Are you free for a quick call next week?”
  8. “I’d like to hear what’s new with you since we last spoke.”
  9. “If you’re around the office next week, want to meet up?”
  10. “Would you be open to a coffee this month?”

These prompts work because they give the other person an easy way to say yes.

Make It a Habit

One of the easiest ways to fall behind in business development is to treat it as something you’ll get around to when you have time. The reality is you’ll never magically find extra hours in the day. If you don’t build outreach into your routine, months can pass without you connecting with the people who matter most.

The lawyers who succeed aren’t necessarily doing more than others — they’re doing it regularly. Consistency keeps you visible and makes it clear that you’re invested in your relationships. Over time, those small, steady touches create opportunities you can’t predict at the start.

Here’s how to put structure around the habit:

  • Block time: Add a 30-minute recurring slot to your calendar and treat it like any client meeting.
  • Work from a list: Choose five people each month to reach out to. Rotate contacts so you cover clients, former colleagues and prospects.
  • Vary your touchpoints: Send a short note, congratulate someone on news, share an article or ask a quick question about their work.
  • Track your outreach: Use a simple spreadsheet or even your Outlook notes to record dates, conversations and follow-ups.
  • Follow up with intention: Don’t let one unanswered message stop you. Try again in a few weeks with something different.
  • Acknowledge progress: Count a reply, a coffee, an introduction or even a thoughtful thank-you as a win. Each one keeps the relationship alive.

When you build this discipline into your practice, outreach stops feeling random and starts creating momentum. A short note today can turn into coffee next month and a new matter down the road. Small steps done consistently are what set the foundation for long-term success.

Timing is Everything

Timing often separates outreach that gets noticed from outreach that gets ignored. Fall is one of the best moments to reconnect. People are back from summer, settling into routines and looking ahead. Clients are reviewing budgets, setting priorities and deciding what will be finished before December and what will carry into the new year.

That frame of mind makes outreach more effective. Messages are less likely to get buried under out-of-office replies and more likely to connect with active planning. Even if your note doesn’t turn into immediate work, it positions you at a time when decisions are being made.

Here are ways lawyers can use timing to their advantage:

  • Budget reviews: Clients finalize legal spend in Q4. A timely message can influence how they allocate work.
  • Deal activity: Private equity and corporate clients often push to close transactions before year-end. Reaching out now can help you support those efforts.
  • Board meetings: Many companies hold Q4 board meetings focused on strategy and risk. Touching base around those meetings can put you into the discussion.
  • Planning for Q1: A coffee or check-in this fall can set you up for a panel, client seminar or new collaboration early next year.
  • Holiday schedules: Reaching out before year-end travel and events makes it easier to secure time with clients.

By aligning your outreach with the natural planning cycle, you increase your chances of being part of the conversations that influence client priorities.

Create a Year-Round Plan

Momentum is easier to keep than to restart. Once you’ve tried the five-people approach for a month or two, give it a simple structure for the year so you cover your network broadly without feeling stretched.

Here’s one way to map it:

  • January: former clients
  • February: referral sources
  • March: industry contacts
  • April: panelists or speakers you’ve met
  • May: people you lost touch with
  • June: warm leads
  • July: collaborators
  • August: professionals you admire
  • September: people you’d like to work with
  • October: people who helped you
  • November: people you’ve helped
  • December: people you want to thank

This rotation keeps you from leaning on the same ten people again and again. It nudges you to nurture groups that often get neglected, like past panelists or people you admire from afar. It also gives each month a theme, which makes outreach faster because you’re not reinventing your list every time.

What to Say

One of the biggest barriers to outreach is simply knowing how to begin. Many lawyers hesitate because they don’t want to sound scripted. The best approach is to keep your message short, warm and tied to something specific. A few sentences are enough to show genuine interest and open the door for a reply. Here are some prompts you can adapt:

  • Hi [Name], I saw your firm advised on [deal]. Congratulations on the outcome. I’d like to hear more about it.
  • Hi [Name], I noticed your fund just closed [round]. Exciting news. Let’s grab coffee soon.
  • Hi [Name], I came across your panel on [topic]. I’d enjoy hearing your perspective on where the market is heading.
  • Hi [Name], I read [article] and it reminded me of our last conversation. Are you free to catch up next week?
  • Hi [Name], I’ll be at [industry event] next month. Will you be there?
  • Hi [Name], congratulations on your new role. I’d love to hear about your priorities as you get started.

Your outreach doesn’t have to be polished or lengthy. A short, specific note shows that you’re paying attention and leaves room for the relationship to develop naturally.

Make It Easy to Say Yes

Reduce the friction in your ask. Offer a couple of simple options so the other person doesn’t have to think too hard about logistics.

If you’re local, suggest a location that’s convenient for them and offer a range like early morning or late afternoon. If you’re not nearby, suggest a short call with a clear time window. If a live chat isn’t realistic, offer to trade notes by email and share one thought to get it started.

Respect time. Call out that you’ll keep it short if that’s the plan. Follow through. If you asked for 15 minutes, end at 15 unless they extend it. People remember when you honor your word. They also remember when you run long.

After the conversation, send a quick thank you with one line that captures what you took from it. If you promised a follow up, send it within a day or two. That reliability builds trust and increases the odds of a next step.

Tie Outreach to Content

Outreach and content work better together than apart. You don’t have to produce long articles every week to make this work. Think in small, useful touchpoints.

If you write a monthly or quarterly client alert, pull out one insight and share it as a short LinkedIn post. Tag the relevant topic, not every person you know. If you record a webinar, clip a 60-second takeaway and share it with a line about who might find it useful. If you publish a longer piece, break it into three short posts and space them across a couple of weeks.

Then connect content to outreach. Send an article or clip to one of your five contacts along with a sentence about why it made you think of them. Ask a simple question to invite a reply. The content gives your message a reason. The message gives your content a relationship.

This approach keeps you visible without adding hours of work. It also creates multiple doors into the same conversation, which raises the odds that one of them opens.

Track What Actually Matters

In law firms and professional services, business development often gets made more complicated than it needs to be. Detailed trackers and elaborate reports may look impressive, but they usually end up sitting unused. What matters most is simple — are your efforts leading to real conversations and opportunities that move relationships forward?

Here’s what I tell lawyers with whom I work to watch:

  • Responses: Are people replying to your emails or LinkedIn notes? A reply means the relationship is still alive.
  • Meetings: Did that outreach turn into coffee, a call or a meeting at a conference? Face time is where real business development happens.
  • Introductions: Did a contact connect you to someone new? That’s one of the strongest signs your efforts are paying off.
  • Work: Over time, did any of these touchpoints lead to new matters or matters expanded? That’s the ultimate measure.

You don’t need to track everything to know if your outreach is working. Focus on a few signals that actually show progress. Review them every few months and look for patterns. If former clients are quick to respond, that’s a sign to keep nurturing those ties. If peers in your industry are engaging with your notes, that tells you those efforts are worthwhile. The aim is to recognize where your time creates the most value and to build on it.

How to Put This Into Practice

One of the hardest parts of business development is knowing whether your efforts are actually working. Lawyers often send notes or meet people at events but then struggle to tell if those touches are making a difference. Having a way to check your progress makes the process feel less uncertain and more rewarding.

The key is to keep it simple. A short record of your outreach is enough — who you contacted, when you reached out and what happened afterward. Did the person reply? Did it lead to coffee or a call? Did they connect you with someone else? Over time, you’ll begin to see patterns in how people respond.

Here are some useful signals to watch for:

  • Replies to your emails or LinkedIn messages.
  • Invitations to meet for coffee, lunch or a call.
  • Introductions to colleagues or others in their network.
  • Engagement with content you’ve shared.
  • Follow-ups where they suggest a next step.
  • Opportunities to pitch, collaborate or join a panel.
  • Matters that trace back to your outreach.

Reviewing these every few months helps you focus on the people and approaches that lead to progress. Instead of feeling like you’re working in the dark, you’ll have a clearer view of where to keep investing your time.

Pay Attention to What Works

The professionals who see the most business development success are the ones who make outreach part of their regular routine. It’s not something they do once in a while, it’s something they build into their schedule and repeat until it becomes habit.

Start with five to ten contacts this month. Spend a few minutes reading what they’ve been working on so your note feels thoughtful. Keep it short and personal. Suggest something simple like a coffee or a call. Then repeat the process next month. The steady rhythm is what creates progress.

Here’s a framework to follow:

  • Start small: Focus on 5 to 10 contacts so the task feels manageable.
  • Be prepared: Read recent updates so your message shows attention.
  • Make it personal: A generic note is easy to ignore. A tailored one is more likely to get a reply.
  • Keep it moving: Suggest a coffee, a call or a check-in. The format matters less than the consistency.
  • Review and adjust: Every few months, notice who responds and what turns into meetings or work, and put more energy there.

Fall is an ideal time to begin. People are back in their routines, setting priorities for the year ahead and open to conversations. Building this habit now sets you up to enter the new year with stronger relationships and a healthier pipeline.

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