How I got over the fear of following up
I used to be afraid to follow up with people.
It feels silly even typing that, but it’s true.
I used to worry that if I followed up with someone, they might find me annoying. Or they might think I’m a micromanager. Or they might feel that I was stressing them out by adding yet another email to their inbox.
Or even worse . . . They might reject me. They might say “no.” I told myself that if I just waited for them to respond, I could hold onto the hope that their answer could be “yes.”
This fear didn’t come out of nowhere. It came from being told that I can sometimes come across as a little . . . intense.
My intensity really helps me as a leader and entrepreneur; it’s what keeps me passionate and driven. But my team and loved ones have helped me see that it’s a strength I need to keep in check—and rightfully so. If I don’t harness it thoughtfully, my intensity can become a weakness. If I’m not careful, I can make people feel like I’m pressuring them.
All of that, combined with my inherent need to make people happy and to be accepted and liked, made following up something I really struggled to do. Every time I found myself waiting for a response to a consequential email, I would think:
Is it too early to follow up?
Do I wait another day? Two days? A week?
Do I even need to follow up?
Can I just wait for them to write me back?
It was exhausting.
Once I noticed this habit in myself, I began to notice it in my team, too. The leader sets the tone, right? Because I feared following up, it meant that those who worked closest with me absorbed some of that fear. That became our culture.
I eventually reached a point where I’d had enough. Aside from being tired of being stuck in a cycle of overthinking, I realized that my fears and insecurities around following up were preventing me, our team, and our business from making progress. I had to get over it.
What finally helped me shift my mindset—and I wish I could remember where I first heard it—was this: Following up with someone is not a burden to them. It can actually be just as helpful to them as it is to you.
I’ll show you what I mean by walking you through a process in our business that often involves following up a time or two: booking me to speak.
When someone is interested in hiring me to speak, they usually have a date in mind. I place a hold on my calendar to protect that date for them while we sort out logistics and decide if we’re going to work together. I take that hold on my calendar seriously: If I have a date blocked, even if it’s not confirmed, I do not book anything over it.
I do a limited number of speaking events per month, so placing a hold means limiting my ability to take on other events. Of course, I could opt not to hold dates, but I don’t roll like that. I understand that my clients need time to figure out whether they can move forward, so I’m happy to help them by holding their dates—for a short while.
The process of turning a held date into a confirmed one is usually pretty quick: two weeks or less. But sometimes, it doesn’t happen that quickly. Sometimes, potential clients are choosing between me and another speaker, or they’re waiting to find out if their budget aligns with my speaking fee, or they’re still deciding on a topic or direction for their event. It can take time to sort out these details and all of the moving parts that come along with an event.
These are the situations where, in the past, my fear of following up would go into overdrive. I was afraid that my behavior would affect the client’s decisions. What if they thought I was being too pushy, and that made them choose another speaker over me? I didn’t want to rush my client, stress them out, or make them feel like I was difficult to work with in case it reflected poorly on me.
But waiting (and waiting and waiting) for responses came at a huge cost. Without confirmed dates, my whole schedule was frozen. I couldn’t accept other events, schedule meetings, make plans. . . . Essentially, our entire business was on pause while we waited for answers.
On top of that, by the time the client finally came back and confirmed the dates, it often meant I had less time to prepare the content for the event, and the team had less time to coordinate my travel logistics. We always got it done, but it disrupted our ability to maintain the internal processes that we know work so well.
Today, I see this situation completely differently. If a client is taking awhile to get back to me with a confirmation, I’m no longer afraid to reach out because I know that doing so is actually helpful to both of us.
Here’s how I think about it: The person on the other end of my emails has a lot on their plate, and booking me to speak is just one small part of their role. By following up, I’m not pestering them; I’m making sure that our conversation stays front-and-center in their minds. I’m helping us stay on track and making sure that my team and I will have the capacity to serve them well, should they decide to partner with us.
I’m also helping myself, our team, and our business because my following-up leads to clarity. Even if the client tells me they don’t want to move forward, at least we know now. No matter what the answer is, it leads to action: If they don’t want to move forward, we can open up those dates again for other potential clients. If they do, we can start planning content and travel logistics. It’s so much better to know than not know!
Seeing it this way has released me from the fear of following up—and since I shared this perspective with my team, it’s helped them, too. Now, we see it as our job to keep the conversation going by following up. That’s how we help a potential client take their request from idea to reality.
More often than not, when we follow up with someone we haven’t heard back from, the response is, “Thank you so much for reminding me!” It’s not a burden or an annoyance to them; it’s a reminder, and it makes them feel supported.
I’ve realized that following up is a form of having a courageous conversation. It involves confronting someone about the fact that you haven't heard back from them, often after they have promised you a response within a certain timeframe. Just like it’s possible to give someone feedback compassionately, it’s also possible to follow up with compassion.
I had a pretty tricky follow-up situation recently that required extra compassion. I had a hold on my calendar for an event, and during the booking process, the client who was considering that date sadly had a death in their family. Understandably, it affected their ability to get back to me on whether we were moving forward with that date.
I had so much empathy for my client. I let our original deadline for confirming our date pass without a thought, but after a couple more weeks of keeping my schedule at a standstill, I had to take action. I reached out again and offered a new deadline for confirming the dates. By the time that date came, though, they still hadn’t reached a decision, and I had to make the tough call to decline the event. Keeping the date held would have affected other event requests and meetings that we were waiting to schedule. At the end of the day, I knew in my heart that I had acted with as much compassion as possible: I’d given them as much extra time as I could before I needed to do what was best for the team and business I am responsible for. The client completely understood.
These conversations aren’t easy, but it’s always possible to have them with compassion, no matter the situation. It’s always in your power to give someone grace—and it’s important to make sure that you consider your own needs, too.
Finding the words for following up can be hard, so in case you’ve struggled with this yourself, I want to give you some jumping off points to show what it can look like. I hope these examples help!
“Hi! I haven't heard back from you about this. Have you received the support you're looking for? Please let me know either way so that I can plan. Thank you!”
“Hi! Have you had a chance to talk to X about Y? I know it’s a really busy time, and you have so many variables to manage. If possible, I would really appreciate a response by next Wednesday. Let me know if that is doable. Thank you!”
“Hi! I am not sure if my emails are making their way to you, and I don’t want to leave you hanging. If you could let me know that you’ve received this, that would really help.”
“Hi! I haven’t heard back about the event, so I will need to release the hold that I have on my calendar. If you still want to move forward, please let me know as soon as possible. If the date you want is no longer available by then, we can look for another one. Thank you!”
Remember, action leads to clarity. Every answer you get, even if that answer is negative, informs the next. Following up is not going to change the answer; if it’s no, it’s no. Wouldn't you rather know for sure so that you can decide what step to take next?
It’s also kind to hold people accountable to deadlines you've agreed upon. If you don’t hear back from someone by the deadline, hold them to it and follow up. Chances are they’ll thank you for it.
Okay, friends, it’s your turn! I’m curious: Do you struggle with following up? If so, what is behind it for you? Has this blog post helped you see it through a different lens? Hit “reply” and tell me more!
Big hugs,
