As a small-business owner for the past 20 years, I have found one activity equally frustrating and fulfilling: following up with prospects and clients.

"Hey there ... I'm just checking in."

"I haven't heard from you in a while ... "

"Are we in a fight?"

It's frustrating because sometimes I don't hear back, leaving me confused about their interests and priorities. When I do hear back, the responses might be noncommittal or vague. Or I might be passed around to another gatekeeper, and another and another, without getting to a decision-maker. I'm also always mindful of striking a balance between being professionally persistent and being positively pushy. And that's all on me to manage; it's not the client's responsibility to tend to my ego or make my priorities theirs.

And yet, following up can be equally fulfilling because when I do hear back, I almost always learn something important.

Like what?

• What's going on for them personally

• What's shifted in their business priorities

• What they're focused on these days

• Changes in their organizational structure

• The budget they actually have versus the one they'd hoped they'd have

• They've moved on to another job, which I usually find out when my follow-up email bounces back

• They appreciate my persistence because the time hasn't been right--until now

All of that gives me important insight into their priorities, needs, and interests, which helps me manage my own expectations and plans. 

Nevertheless, it can be easy to fall out of the follow-up habit. Considering that following up takes valuable time, can feel boring, and can hurt our egos, it's little wonder many of us avoid it. It can often feel like Schrödinger's cat: Until you follow up, the business is simultaneously lost and won. Why mess with the balance of probabilities with an actual follow-up?

Because without follow-up, you will not build a deeper relationship with prospects and clients. You will not know what questions still need answering or concerns still need addressing. You will not get the valuable feedback you need to refine your offerings. You will not learn how to skillfully manage resistance without hurting the relationship. You won't learn when to keep going and when to back off. You will not know when and what to upsell or cross-sell. And you won't get referrals to grow your business.

Here are four ways to stay motivated when it comes to making follow-up a habit:

1. Regard follow-up as a reflection of who you are, not just what you do

Yes, following up requires a series of mindsets, skills, and tasks, but it also requires you to see yourself as the kind of person who does this work. When I find myself resisting or delaying follow-up, I'll remind myself: "I am the kind of person who cares about my professional relationships" or "I am the kind of person who does challenging things" or "I am the kind of person who finishes what she starts."

I also remind myself, "I am the kind of person who treats herself after doing something she doesn't love doing"--and then I have a cookie, buy fresh flowers for myself, or watch an episode of Top Chef.

2. Make follow-up a personal conversation

Following up doesn't have to be a series of boring emails back and forth. Use what you know about your prospect or client to show them that you see them as a person, not just a potential paycheck. How does this serve you, too? You'll feel like you're having a conversation with a friend rather than plugging away at a dull task.

I have one client who loves to travel--as do I. Most of my follow-up emails to them include an update on where I've recently been, a question about where they're heading next, and a request for some travel tips for someplace I know they've visited already.

I have another client who attended Ohio State University, whereas my son and I both attended its top football rival, the University of Michigan. My follow-up emails include a little bit of good-natured trash talk, and my client responds in kind.

Other clients have also expressed appreciation when I reach out to wish them well on Muslim, Hindu, or Christian holidays, even though they know I am Jewish.

3. Use a "body double" to get the job done 

If the prospect of spending hours alone in front of a computer doing follow-up sounds terrible to you, you're not alone. I am right there with you. So, whenever possible, I don't do it alone. I recruit a friend or colleague to be my "body double," where you work in the physical or virtual presence of another person who may be doing their tedious project.

The benefits of body doubling include reduced feelings of isolation, decreased procrastination, and increased accountability since you will have committed to your "double" to do your work. This could be a colleague or a friend, or you can even do this as a team and make it a friendly competition.

4. Brainstorm worst practices--and then do the opposite

In my work with leaders and teams who need to get better at business development, I often take them through a "reverse brainstorm" on the successful mindsets, habits, and skills of salespeople. One prompt is: "Imagine your number one goal is to ruin your client and prospect relationships. What can you do to make sure you never sell another product or service to your existing clients, and never convert another prospect?"

Answers might include "disappear after the initial contact," "mix up or forget important details, names, and companies," "send daily emails, hourly texts, and call them in the middle of the night to show clients they're always on your mind," "ignore boundaries, social cues, and politeness," and "tell them how much money you need to make this quarter to pay your bills and guilt them into buying something."

While, hopefully, you're not doing any of these things, you might notice some themes that are worth investigating. For example, while you may not disappear completely after an initial contact, perhaps you are waiting too long to follow up. Or while you might not forget important details about a client, you might not be actively showing them that you remember what's important to them.

Following up with clients and prospects may not be the most rewarding, fulfilling, or fun part of your job. But by making it a little more engaging and a little less tedious, you can reap the benefits of creating long-term, successful, win-win relationships.