Direct answer: Sales leaders fail their teams when they criticize outreach tactics they'd never tolerate being used on themselves, then let their own reps do the exact same thing. Two practices fix it: get on the phone regularly, and never allow your team to do what wouldn't work on you.
I once watched a public back-and-forth on LinkedIn between a group of CROs and VPs of sales that struck a nerve. One CRO posted a screenshot of an email from a business development rep, tearing apart the outreach technique. Some of the criticism had merit. But if that same CRO searched his own inbox, he'd find his own BDRs sending the same kind of message. That contradiction says a lot about where sales leadership goes wrong, from first-line managers up to the C-suite.
Leaders Who Stop Making Calls Lose Their Read on the Business
Even the most experienced sales pros lose their edge if they stop using it regularly. Leaders need to understand not just the message their team delivers, but how prospects actually respond to it. Getting on the phone surfaces roadblocks a team won't always volunteer in a one-on-one. It also means you'll fail sometimes, which is a good thing. It shows your team how to keep going after getting shut down, and that mistakes are survivable. It shows them the work isn't beneath you. Nothing motivates a team faster than a leader who wants to be on the phone with them.
Don't Let Your Team Do What Wouldn't Work on You
This is the contradiction that should bother every sales leader. You can see clearly every problem that automation creates in outreach, canned emails, poor social touches, junior reps cold-calling with no context, and still let those same problems happen inside your own team. If a canned email wouldn't work on you, it isn't going to work on a prospect either.
To actually check this, leaders should be doing the following on a regular basis:
- Listen to call recordings
- Read a full cadence of emails sent to a single prospect
- Role play with the team
- Listen to calls in real time
- Get on the phone themselves
- Talk to a current customer
- Analyze the data and actually use it to guide decisions
It's easy in sales leadership to get busy enough that you forget the fundamentals that built your own career. Technology lets salespeople move through the process faster and reach more prospects, but it also makes it easy to just hit send on a canned email without thinking about that specific prospect. Your team is a reflection of you and your style. Teach it that way.
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See Sales Leadership TrainingFrequently Asked Questions
What is the biggest mistake sales leaders make with their teams?
Criticizing outreach tactics in others that their own team does every day. If a canned email wouldn't work on you, it's not going to work on a prospect, and it's not fair to blast someone else's team for the same thing yours does.
Why should sales leaders still make cold calls themselves?
Getting on the phone keeps a leader's read on the market honest and surfaces roadblocks the team won't always volunteer in a meeting. It also shows the team that failing on a call and getting back up is normal, not something to hide.
What should leaders actually do to check their team's outreach?
Listen to call recordings, read a full email cadence sent to one prospect, role-play with the team, listen to live calls, get on the phone themselves, talk to a current customer, and actually use the data to make decisions.