Leaders Should Be Direct, Not Harsh. Here’s the Difference.

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John Hall
John Hall


A few months back, I had a heart-to-heart with an editor on my team. "Your work is great," I told him, "but we have to prioritize volume."

sales manager delivers direct feedback

I can’t blame this person for being a perfectionist. If anything, it’s an important quality in an editor. But as we approached capacity, I had to be clear: Not every piece of content we create can be a masterpiece.

Together, the editor and I looked at examples of "good enough" content. I promised him I’d hand him opportunities on which he could flex his creative muscles, and he assured me he saw my perspective. We ended the conversation on a positive note, satisfied we were on the same page about our business needs.I think he’d agree: Our conversation was direct, not harsh, and the whole team is better off because of it.

→ Click here to download leadership lessons from HubSpot founder, Dharmesh  Shah [Free Guide].

Focus On Being Direct, Not Harsh

Whether a writer or a salesperson, every employee is a work in progress. For the sake of their personal and professional development, they need clear, direct feedback. The trouble is that some leaders take "clear, direct feedback" to mean something else entirely. They worry that they won’t be heard unless they’re confrontational and abrasive.

That goes double when we’re talking about providing feedback in a virtual context. When we email or Slack feedback to others, our tone is lost to our phrasing; what would sound encouraging or simply neutral with the right hand gesture or aside can become harsh or dismissive in a digital format. Even a slight shift in punctuation such as "This looks like the right track" versus "This looks like the right track?" can alter your comment, rendering your feedback unclear and unhelpful.

Think about employee relationships like any other in your life: When your partner overspends on your credit card, does it help to storm in, yelling about how irresponsible they are? Of course not. Instead, you look at your finances together and talk about what’s within your budget and what isn’t.

That’s a better way to approach having a difficult conversation, and it’s how effective leaders bring out the best in their salespeople.

If you struggle with being too direct, check with a friend. Jeff Winters, CEO of Sapper Consulting, is one of the best sales experts I know. I typically give him a quick call for feedback before I come into a situation with my "direct" hat on. Find someone who you trust to be a checkpoint when you need it.

Begin with empathy.

Of course, it’s easy to look back and ask, "Did I handle that one-on-one the right way?" But when you’re planning ahead, the best way to think about the conversation is from the other person’s perspective.

That’s the work of empathy. And when you’re feeling frustrated with someone, it’s hard work. To get in their shoes:

1. Map Out A Plan

HubSpot recommends empathy mapping as a way to get into the mind of your customer. But it works surprisingly well for thinking through employee management matters as well.

The key difference is replacing the customer’s persona with that of your team member. Imagining the conversation you’re planning, ask yourself: What does the employee think and feel? What does she hear? What are their pains and gains?

Thinking through those questions can help you be measured and clear in your communication.

2. Say "yes, and… "

One of the best pieces of improv advice for aspiring comedians is to say "yes, and…" to their partner. The idea is to build on what the other person communicated while adding your own elements — you’re agreeing to what the other person said and building upon it, showing you’ve truly listened to him. Constructive conversations can only happen when both parties in the conversation feel heard.

3. Put Yourself In the Listener’s Shoes

Perhaps I shouldn’t say this, given that I moonlight as a keynote speaker, but it’s the truth: Half the value of bringing in an external speaker is simply that it reminds you how to be a listener rather than a leader.

The key is choosing a leadership speaker or sales speaker whose expertise aligns with the issues you’re facing. You always have room to grow, just like your employees. Learning how they’re hearing you or responding to what you bring to the table can push you to create more space for back-and-forth idea sharing in one-on-one conversations, where leadership is perhaps trickiest.

Productive conversations start with empathy. But concrete examples and explanations are what create clarity.

Be Concrete

The goal of direct feedback should be to help develop a desired skill or behavior for your team member. If you can’t clearly illustrate the behavior or outcomes you’d like to see, that’s going to be tough. With writers, it’s about showing articles and talking through edit times. But what about in sales? Here are a few tips to help you articulate desired behavior for salespeople:

1. Try It Together

What’s an appropriate example depends heavily on the subject of your feedback. The principle, however, is the same — show your salesperson how you’d approach the situation.For example, let’s say that someone isn’t adequately preparing for their calls. Take the next one together, showing them the notes you took about the company or prospect.

If they aren’t getting granular enough in their proposals, model the level of detail you’d like to see around one type of deliverable; ask them to do the same for the rest.

2. Stay Organized

We recently started using project management software called Teamwork to improve our collaboration and to keep the team organized. Getting our salespeople on the same page with projects has done wonders for our communication.

If you can’t afford to implement a new tool, start with Google Docs for tracking project deliverables and due dates. Whatever your system, you need a central place to store project details.

3. Consider Time Tracking

To be clear, I don’t require my team to track their time. From my perspective, the time and trust costs outweigh the benefits. But if you want to encourage a salesperson to spend their time differently, it helps to know how they’re currently spending it.

One middle-ground solution is schedule analysis. Calendar, which I invested in, is in the process of developing data visualizers to display how and with whom users spend their time. Salespeople spend most of their days on calls and in meetings, so automation can give a good view of how they spend their time.

How you conduct the conversation is important. Good salespeople know the importance of a follow-up, though, and so should you.

What To Do Down the Road

Direct feedback works most of the time, but some salespeople might need a second nudge. Here’s how to deliver it in a firm but respectful way:

1. Give Them A Chance to Win

Salespeople tend to haveType-A personalities. When they’re given an opportunity to rise to the occasion, they typically do.

For instance, if building rapport was the issue, introduce the salesperson to someone they’d click with. Suggest those similarities prior to the call. Give them a chance to connect on their own turf.

2. Encourage Self-Reflection

I begin every performance review by asking for self-evaluation. Why? Because most people want to see themselves make progress. And whether or not they’re honest with you about it is a key indicator of whether or not they’re worth your continued investment.

Ask for quantitative and open-ended feedback. If close rate is the issue, how much progress does the salesperson feel they made on a scale of one to 10 with one representing a 10% improvement and 10 indicating an ideal solution? Encourage them to explain that score to you so you can understand their thought process.

I’m neither a perfect leader nor the world’s best salesperson. But I’ve been doing both for long enough to know that mean-spirited feedback doesn’t work. Anger doesn’t work. What does work? Clear, respectful communication about the issue, and nothing less.

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