JD Miller

I was as SE in the early 2000s, when demoing a web tool meant you had to first start up a database, then a web server, then open a browser to begin the demo. Invariably, something was going to crash. Having a local copy or screenshot version worked just as well. The pages loaded faster, and it kept the audience on track (no “what happens if you click on THAT?”). Your audience should trust that the software actually works - use a screenshot to show highlights that reinforce your main points.

Set expectations quickly. Often a new sales role is open because of two things - the previous rep in the territory didn't achieve their goal AND they were unable to articulate the true state of the business. As you adopt a new territory, quickly assess the pipeline and give a clear-eyed view of what's "real," what's not, and what to expect when as you get things back on track. Often, new sellers I hire want to come in and say "there's nothing, here, and it's going to take 3 quarters until I sell anything." That's not good either. Instead, think about what visible, incremental progress you can make each week/month and tell us what you can be held accountable to - calls made, meetings set, and eventually - sold deals.

As you listen, be sure you’re asking questions that diagnose the disconnect. Why did they buy the product? What did they think it would do for them? What did you think it would do for them? Can you create the business benefit they expected in a different way? If not, did you oversell, or has their need shifted. Understanding the context will help craft a way forward that works for both parties.

The beauty of virtual interviewing is that you can do them with little investment - but that doesn't mean you shouldn't prepare! Your interviewer will only have your voice and words to make a judgement about you, so contrtol eveything yuo can - get away from screaming kids, barking dogs, background TV, and just surround yourself with silence. A benefit to phone interviews is you can have a lot more supporting material than you'd bring to an in-person interview. So have your resume, key talking points/stories you want to tell, and important notes about who you're meeting with. Use a pen to check off each "must tell story" as the interview goes on to stay on track!

The average tenure of a sales leader is 18 months in role. I believe that forecasting the business properly is even more important than "hitting the number." Owners, shareholders, and Board members can adapt to lots of things. Given enough time, they can help adapt to a team that is not going to hit the number that was originally planned. The importance for the CRO is to give everyone enough time to adjust to whatever the number ultimately will be. Ideally you want to be able to predict where the team will land within 5% - missing a too-high forecast creates a need for cost cutting, while overshooting a too-low forecast means you missed opportunities to invest. Like goldilocks, you want to forecast "just right."

Feedback really needs to be timely! Often, folks are afraid of conflict, and so they don't give any feedback until they've got 10 or 15 things all piled up - and it's then such an emotionally-fraught conversation, it ends poorly. Being in the habit of giving feedback - good and bad - all the time, as soon as something has happened is a low-stakes way to get people comfortable with these conversations.