Inspiring creativity

Hey Reader — my team has struggled getting responses, especially over email too. We’ve tried to optimize for the basics: relevance based messaging, persona based sequences, etc.

Still no lift.

I showed my team the data so it was really clear that what we’re doing isn’t getting us to where we want to be. I also showed them how doing more activity alone to get to our desired results would be brutal. 

Then, I shared with them that we’re going to need to do something different — something creative even — to try and get more conversations going and asked them about different paths we could explore to close the gap.

For some teams, going through these steps — showing the data and asking for their ideas — can be more than enough to get their creative juices flowing. 

But, if your team is quiet and isn’t sharing a lot, it might be because they don’t know what “being creative” means. Or, they aren’t confident in their ideas because they haven’t given them a fair try yet.

If your team sounds like the latter, laying out a few accessible examples of what “being creative” means can be really helpful. For example: 

• Channels: Using social as a way to connect rather than only using email / calls
• Content mediums: video outreach, audio notes on LinkedIn if connected, etc
• Relevance: Some reps may not be researching or finding points of relevance at the account +/or prospect level. Exposing reps to different types of relevance points – personal interests, hiring, alma mater, etc – and how to tie that into outreach is another expression of creativity
• Personality in outreach: Some reps make jokes, use analogies, send poems, and more. Encouraging reps to infuse their personality into their outreach is another way to stimulate creativity on the team.
• Process: Use ChatGPT / Gen AI to help reps in a specific area of their process, i.e. researching an account, crafting an email, etc, and/or use Gen AI to help them find examples of creativity, i.e. have your reps submit the prompt ‘what are ways I can be creative as a sales rep?’ in ChatGPT to help get their creative juices flowing.

Not only will your reps see that “being creative” is much simpler than they may have thought, they’ll also see that “being creative” can mean a wide range of things.

But remember, there’s more than just telling your reps to be creative and pointing to different ways that creativity can show up.

You also need to model creativity and recognize your reps when they take creative action.

Model creativity 

If you don’t model creativity for your team, you probably won’t see them modeling creativity either.

One way you can start modeling creativity for your team is through adding a little pizzazz into your team meetings.

For example, I recently switched out our Monday morning status update meeting with a game day Monday meeting. We’ve done trivia, Cards Against Humanity and Song Association. The benefits have been great:

• It helps set a fun tone for the week
• It supports building team camaraderie
• The reps look forward to it — this is huge because it’s a Monday Meeting
•  It also helps big time IMO for cultivating psychological safety so reps are more open to taking creative risks

You can also demonstrate creativity by getting into the work with the team. For example, let’s say you have a standing prospecting meeting with your team to collaborate on breaking into a target account in one of the reps’ books of business. If you sense that your rep isn’t being as creative as you’d like them to be, that’s where you can step in and show them what creativity can look like and how you would go about executing on it.  

True story: I created a prospecting video with a SnapChat filter where my eyes and mouth were on the body of a frog for one of my reps to use since they were hesitant about leveraging video. The reps got such a kick out of the video AND they no longer had an excuse to not try something creative out. 

Another great reason to get into the weeds with your reps on how to be creative is because you’re walking the walk. Too often, managers ask their people to do things that the manager hasn’t done or would never do. If your people don’t believe that you would do it, they won’t even think about giving it a try. However, if you’re side by side with them, showing them that you’re not above being creative, they’ll be more likely to give it a shot.

Recognize creativity

Positive reinforcement is such a great tool to employ when trying to get your reps to try something new. This is especially true when you’re trying to motivate your team to try out more creative (*cough* anxiety inducing *cough*) ways to engage their prospects. To get started, consider:

• Giving shoutouts in your team channel when someone takes a creative risk
• Celebrating reps when they’re able to produce a desired outcome from taking that creative risk
• Creating a SPIF to compensate or reward reps for trying creative approaches

Most folks appreciate being recognized for their effort and will adjust their behaviors to be on the receiving end of such recognition.

If you haven’t already tried this out…I’d encourage taking a shot at it for a few weeks and seeing how your team responds. 

Wrapping up

There are so many ways that teams can be creative — whether it’s using different content mediums, leveraging new technologies to become more efficient, or finding new approaches to old processes. 

By letting your team know that there’s more than one way to be creative, you’ll see them lean into what creativity means for them more. And, if you’re willing to show your expression of creativity, you’ll have a much better time at getting your reps to try out new and creative approaches.

Lastly, today’s newsletter was inspired by a question a reader posed. It’s always an honor to get questions from you. If there’s something you’re really curious about or are struggling with when it comes to people leadership and management, holler my way! Your question may inspire another advice column newsletter that will not only help you, but all the other folks out there who may be struggling with the same issue.

Visual of the Week

One of my favorite things about being in management is creating a culture of iteration and innovation. In building this kind of culture, we embrace an attitude of gratitude when things don’t work, because that means we’re one step closer to finding what will work. And, in these cultures, we respect and recognize progress over perfection…seeing excellence as a result of continued effort, rather than a quality that people have or don’t. 

Weekly Reminder

✨ “The more we value things outside our control, the less control we have”. – Marcus Aurelius  ✨ 

If you’ve ever managed someone, you probably know how hard it can be to get people to focus on things that are in their control. I’m loving this Marcus Aurelius quote and will be adding it into my leadership talk tracks whenever reps get overwhelmed by things outside of their control.