Sales Leaders: Schedule a 90-Day “Heart-to-Heart” | Sandler Training Skip to main content

There’s a tendency on the part of some managers to expect their new sales hires to “hit the ground running.” Often, managers justify this expectation by telling themselves that they only hire “self-starters.” Both of these assumptions are part of an ineffective hire-and-forget approach, one that can and should be remedied by a solid onboarding plan that’s based on a series of monthly one-on-one coaching conversations. I call the most important of these conversations the “90-Day Heart-to-Heart.”

Make no mistake. The hire-and-forget model costs our organizations both revenue and talent, and it begins with the unrealistic expectation that a salesperson should be able to “hit the ground running.” All too often, we simply don’t take the time to structure the first weeks and months of a new salesperson’s relationship with our organization, or set clear expectations about what should happen when in order for the person to succeed. This failure to plan is a major lost opportunity. Why? Because there’s never going to be a time when the salesperson will be more motivated to touch all the bases and do what needs to be done to succeed than the first 90 days on the job!

There are a lot of possible approaches to a successful onboarding plan for a new sales hire. What follows is one model that has proved successful, but that may need to be adapted to match your industry and your selling cycle. Note that the “90-Day Heart-to-Heart” conversation it points toward is the not the end of your monthly coaching sessions with this salesperson! These should be ongoing.

MONTH ONE: LEARNING. This month is all about learning the sales process and the product/service. Your best option is to consider the salesperson more of an intern during this first month, allowing him or her to spend as much time as necessary with the key people, up to and including you, who can help the new hire master the basics about what you sell and how you sell it. Although it’s fine, and highly recommended, to give learning assignments and do assessments about how well these assignments have been understood, you shouldn't set revenue expectations for the salesperson this month. You should, however, set clear learning expectations, and set up appropriate training, reinforcement, and roleplay. At the end of MONTH ONE, you should set up a one-on-one coaching session in which you get a clear sense of where this new hire sees himself or herself going career-wise over the next year or so, discuss the results of any assessments, and take this salesperson’s temperature on how the first 30 days have gone. Listen to what comes back. Remember that this coaching session is meant to be a conversation, not a monologue!

MONTH TWO: LAYING THE FOUNDATIONS. During the second month on the job, the new hire should have activity targets, but not revenue targets. The idea here is to let the individual get his or her feet wet, and start actually executing, at a daily level that’s realistic, the documented, repeatable sales process that your organization follows. So if your sales process involves outbound calls, you’re going to set appropriate daily targets for those; you’re going to do the same for all of the activities within your sales process that eventually deliver revenue. This may take some experimentation and revision. Be prepared to have ongoing discussions this month about how these daily activity targets should be tweaked. Note that the emphasis here is on setting up a daily pattern of behavior, not on creating a specific revenue outcome. At the end of this month, your one-on-one coaching session will focus on how the initial numbers look … whether the new team member is getting the support he or she needs … and what the target for account acquisition should be, one month out. Work those numbers out together. The assumption here, of course, is that the person is now comfortable enough with the sales process, and with you, to make an informed estimate of the revenue and/or prospect development he or she will be willing to commit to have on the table thirty days from now.

MONTH THREE: LIFTOFF! At the end of Month Two, the two of you collaboratively set a goal to have a certain amount of business either closed or in the pipeline. Month three is when that happens … or doesn’t. The one-on-one coaching session you have at the end of this month – your 90-Day Heart-to-Heart – is therefore the most critical discussion yet. If the person is on target at the end of Month Three, or ahead of target, congratulations! You can use this session to identify exactly what’s working, reinforce that, identify any potential trouble spots, and look for the best ways to support this salesperson over time. Of course, you’ll want to offer plenty of appropriate praise and encouragement for the great start.

But what if the new hire is not yet close to hitting the target? Then it’s your job to use this coaching session as a tool that can help you each to identify exactly what the obstacle is. Again, this is a discussion – not a lecture. One good way to open it might be:

“Jim, last month was all about laying the foundation. You were starting to make the calls, and I know your call volume and your other activity levels were looking very strong. And then at the end of that month, we set a goal to have a certain amount of accounts identified and in the pipeline – we wanted to have X number of accounts closed, and Y number of accounts qualified and in the sales process with us. So the last time we met, you indicated you thought this was a reasonable goal, and I'm just curious, given that we’re still a little bit short of that, how do you feel about where we are?”

Then – this is critical – let Jim talk. Let him share exactly where he feels he is at: what he’s done well, and what he’s done poorly; where he’s feeling frustrated and where he’s feeling optimistic. It’s not a heart-to-heart discussion if you don’t each get to say what’s on your mind! So listen carefully to everything Jim shares with you.

One important thing you’re looking for during this discussion is how willing to learn and how coachable Jim is. If you’ve done your job up to this point, he should be comfortable taking full responsibility for where he is right now and what has to happen next, and he should be open to a pragmatic discussion about how he can improve. All your previous coaching conversations should have established that dynamic. If you’re not getting that kind of response, if Jim’s first response is to play the blame game or point toward outside obstacles, that could be a sign that your coaching process is off, or even that you may have hired the wrong person!

Another vitally important question you’re trying to answer – together – is where the obstacle really lies. At the end of the day, there are only three issues that could be in play: Jim’s attitude, his effort, or his level of skill. These require very different conversations, so the part where you work together to identify which of these is standing in the way perhaps the most important element of you 90-Day Heart-to-Heart. What you say might sound something like this:

“So Jim, we’ve identified that there’s a gap here between where you are and where you want to be. My question for you is: What do you think is standing in the way of you closing that gap? Do you think it’s a question of attitude … or is it the amount of effort you’re putting in … or is it a skill that we haven’t gotten you up to speed on yet?”

Again – listen carefully to what Jim shares with you, and take his insights seriously. Don’t assume you already know the answer – and don’t prescribe a solution before Jim has had the chance to share what he thinks is going on. A classic mistake is to assume that the problem is related to effort – when in actuality there is an underlying problem about Jim’s attitude toward the job, the company, the market ... or Jim himself.

The real victory of the 90-Day Heart-to-Heart comes not when you set up a plan for getting Jim to where he wants to be, but when Jim does … and he asks you for your opinion on whether or not that plan is viable. After all, he’s much more likely to implement a plan that he’s created than one that you have!

Don’t assume your sales hires will or can “hit the ground running.” Give them all the support you can during those critical first 90 days … and have a Heart-to-Heart coaching session with them before you move forward to the next 90 days.

Read these blog posts to learn more leadership best practices and how to effectively coach your team.

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