6 Lessons from my First Year of Selling

Sales enablement has been part of my job for over six years now. I’ve worked with sales teams training them on social media, email communication, and implementing the tools I create for them. I’ve shadowed sales reps to see their methods in action and report on the success of different strategies. Until this past year, I hadn’t actually had to do the outreach myself. Even when I hit send, it was someone else’s name on the email. It was someone else who would handle the next step even if I’d mapped out the course. Actually taking my own advice taught me a lot about what works and what doesn’t.

Things that work 

Follow-ups

Following up with a message, email, or phone call has always been one of the biggest things I recommend for sales reps. Sending follow-up emails can increase your overall response rate by 40%(1). Knowing how successful it should be made it one of the first things I included in my outreach to prospective clients. It has been by far the most important part of my success in the last year. 

Whenever I send an email to a client that requires a response or action, I put a follow-up alert on my calendar for a week later. If I am talking with someone and they seem interested but now is not the right time, I set up a reminder to reach out to them in a month. 

Simple, specific asks 

While it may seem obvious that being direct and transparent is the best way to get anything done, it turns out keeping things simple was the real game-changer for me. Instead of saying “Let me know if you’d like to meet sometime” I would say, “I would love to set up a quick chat, feel free to book a meeting on my calendar” with a link to my Calendly so they could set it up then and there. When I am wrapping up networking meetings, rather than saying “let me know if you know anyone who needs any marketing support” I say “Let me know if you know anyone who needs help with their LinkedIn profiles or anyone who needs B2B social media help”. 

Easy next steps 

Every email I send to a client has the next steps in it. That might be a link to schedule a meeting, a list of things to send me, or even just a heads up that I will be reaching out again later. I have worked with enough busy people to know that if that next step isn’t easy and clear, it’s less likely to happen. Even if I think it’s obvious what they need to do, I make sure to lay it out for them. Making someone figure out the next step to keep the ball rolling just means more work for them. By laying out what needs to happen to move forward I make it easy to work with me, making the client more likely to want to. 

Things that didn’t work 

Long messages 

Anyone who’s had to write marketing materials knows that shorter is better 9 times out of 10. Still, when it came to my own outreach I found myself doing exactly what I advise people against - trying to tell the whole story in one message. I would find a new client or even a possible partner and I would find myself messaging them everything about me, my business, and why we should work together. Any time I was unable to stop myself from sending a full book’s worth of information in a message, the response rate would drop and those who did respond were more likely to say no to my ask. 

Instead, I found that keeping messages short and taking it one step at a time was far more effective. Starting the conversation by simply pointing out things we had in common and offering to connect on LinkedIn made potential clients far more likely to accept my invitation. After that, I could follow up with reasons I thought we should talk or something I admired about their work. These kinds of messages, building the story over time, has been something I have recommended to sales reps for years. Actually putting it into practice showed me just how much more effective it was, even when it felt counterintuitive. If I want someone to do something, shouldn’t they have all the information upfront? Seeing it in practice I realized how important building trust can be. Putting everything about my business out there and starting with the bigger ask was assuming trust that wasn’t there. Building that up slowly and progressively– with a connection request, then some context on how we can help each other, then asking for a meeting, and so on– always led to a stronger connection.

Generic calls to action 

When emailing people or messaging them on LinkedIn it was tempting to put something like “let me know if you need anything” or “if you are interested in connecting, let me know”. Even with friends in my network, I was tempted to say, “let me know if you have anything you want to work on together”. I wouldn’t get a response to something like that. 

Things went differently when I provided clear, specific intentions. “If you know anyone who is considering moving into consulting and wants help with their LinkedIn, point them in my direction” or “if your business needs help with B2B social media marketing, I can help support any projects that might come up.” When I message a new connection after they accept, I say “I would love to set up some time to chat about your work with XYZ and how we could work together”. This easy shift in communication garnered a dramatically greater response.

Flexible to a fault - too many options 

When I first started reaching out to my network and reaching out to new people about what I was trying to do, I would try hard to be flexible on how I could support their business. I would tell people that I could help with any B2B marketing communications, even B2C if they needed it. I would talk through a million different ways I could work for them. 

Any good marketer can see this problem coming a mile away. It’s like an email with six calls-to-action instead of one. I tried to be open to any projects they might have. It’s a classic example of the paradox of choice: 2 choices make people more likely to buy, 10 choices and it’s too much (2).   In the end, those opportunities were way more likely to fall apart or get pushed off someone’s list of priorities. 

 Instead, when I came in to offer specific solutions, I would recommend we do X or we start with Y. I found that clients were much more responsive to these fewer, more tangible options. While it seemed logical to be open to supporting their business in whatever way they needed, I was actually putting the work of figuring out how to use my skills onto them. The last thing a busy professional wants is another task on their to-do list when what they need is someone to take things off their plate. 

The last year has been an intense learning experience. So much of it has been an out-of-the-frying pan into the fire situation. Putting these small adjustments into practice may look inconsequential but any entrepreneur or salesperson will take you it’s the little things that matter. These changes make my business into that proactive, effective, and demonstrable opportunity that stands out to professionals looking for just that.

Looking for more articles like this, sign up for our newsletter.

1 - https://woodpecker.co/blog/follow-up-statistics/ 

2 - https://cxl.com/blog/does-offering-more-choices-actually-tank-conversions/