"Uncomfortable doesn't mean bad, uncomfortable simply means you're doing something you haven't done before."

Joe Vitale

I encourage CEOs and Presidents to ask themselves a tough question... Are you creating an environment where your salespeople are allowed to be uncomfortable enough to grow?

All too often, leadership says it wants growth while simultaneously protecting people from the very discomfort required to achieve it.

Tenured salespeople are allowed to operate the same way, avoid difficult conversations, skip training, resist coaching, and lean on yesterday’s success because leadership doesn’t want to rock the boat.

Keeping people comfortable doesn’t keep a sales team healthy, it can quietly stunt their growth.

When leaders tolerate stagnation in the name of harmony, they aren't protecting their salespeople; they're protecting the status quo.

Real sales growth requires discomfort, and new skills feel uncomfortable.

Accountability feels uncomfortable, as does challenging a salesperson’s beliefs feels uncomfortable.

Asking better questions, pursuing bigger opportunities, having difficult client conversations, learning new technology, and being coached can all create friction. That friction is often where growth begins.

CEOs have a responsibility to create a culture where discomfort isn't viewed as failure but as evidence that someone is stretching beyond what they already know.

If you continually make it easier for your salespeople to stay comfortable, don't be surprised when revenue, client relationships, retention, and personal growth eventually become stagnant.

You cannot demand a growing sales organization while creating an environment that makes growth uncomfortable for leadership.

As we kick off our journey together, here's something that will certainly stir the pot... What if leadership, not the sales team, is allowing complacency to become part of the culture?

This might just make some of you uncomfortable, as I ask those that this applies to... Why are you allowing this to happen?

You have salespeople who have been with the company for years, if not decades. They have relationships, they know the customers, they know the products, they know the market, they've been around long enough to have seen almost everything, and yet...

• Their prospecting hasn't materially changed (when have they prospected?)

• Their client conversations haven't materially changed

• Their preparation hasn't materially changed

• Their follow-up hasn't materially changed

• Their ability to uncover new opportunities hasn't materially changed

They're still relying on what worked five, ten, or even fifteen years ago, and when someone challenges them, the response is often predictable... I've been doing this for a long time.

The uncomfortable question for you all... What exactly have you been doing for a long time?

There's a massive difference between having 20 years of experience and having the same year of experience repeated 20 times.

Conversation amongst salespeople is often aimed directly at the salesperson.

• Practice

• Prepare

• Get uncomfortable

• Develop your skills

• Build better habits

• Stop relying on seniority

• Keep growing

I agree with all of it, but I've been thinking about something deeper... Who created the environment where salespeople can stop doing those things without meaningful consequences?

CEOs, This One Is For You

Professional athletes don't get to say... I've been playing for 20 years, so I don't need to practice anymore.

Imagine a professional football team where the veterans stopped practicing fundamentals because they had been around too long.

Imagine a baseball player saying... I've hit thousands of baseballs, I'm good.

Imagine a championship team deciding that film study, preparation, conditioning, and repetition were only necessary for younger players.

It would be absurd, yet executives and their leadership team routinely tolerate exactly that behavior in sales.

You all chalk it up and use the following to justify...

• They have experience

• They have the relationships

• That's just how they sell

• They've always done well for us

• We don't want to rock the boat

There's a point where protecting someone's comfort becomes expensive, very expensive.

Complacency doesn't always show up as an obvious crisis, it shows up quietly.

• Fewer prospecting conversations

• Fewer new relationships inside existing accounts

• Fewer meaningful business conversations

• Fewer cross-selling opportunities

• Few more customers who quietly begin talking to competitors

• Few more salespeople who stop stretching

Eventually, you all look at the numbers and wonder... Why aren't we growing like we should be?

Maybe The Problem Isn't Your Salespeople

Is it possible that the deeper problem is what leadership has been willing to tolerate?

It's easy for you all to point at a salesperson and say...

• They aren't prospecting

• They aren't developing enough relationships

• They aren't asking enough questions

• They aren't growing existing accounts

• They aren't bringing us enough new business

Here's the question I'd be asking first... What have you, as the CEO or President, created that allows that behavior to continue?

• Have you established a clear standard?

• Have you coached to that standard?

• Have you measured it?

• Have you inspected it?

• Have you reinforced it?

• Have you rewarded it?

• Have you addressed it when the standard isn't met?

Or have you quietly accepted the behavior because confronting it feels harder than living with it?

Accountability isn't about beating people up, it's about caring enough to help people become better.

The Don't Rock The Boat Culture

Unfortunately, this type of culture is playing out all too often. What's alarming is everyone in the company knows it's happening.

The CEO knows, so does the president, the sales leaders, the sales team and sometimes even the clients know.

• Everyone knows which salesperson has become comfortable

• Everyone knows who isn't prospecting

• Everyone knows who is living off a handful of legacy accounts

• Everyone knows who doesn't prepare

• Everyone knows who doesn't follow through

• Everyone knows who could be doing much more

And yet... You all don't want to rock the boat. Why?

• Because the salesperson has been there forever

• Because they have relationships

• Because they're a nice person

• Because they used to be a top performer

• Because leadership doesn't want to lose them

• Because confronting the issue could create conflict

Here's what I believe... Things are good enough, simply good enough.

Good enough doesn't usually destroy a company overnight, it simply prevents the company from becoming what it could become.

Comfort Has A Cost

My friends, you can either be comfortable and stagnate or stretch yourself to become uncomfortable and grow.

A salesperson's comfort affects their territory, however; your comfort affects the entire company.

When a salesperson avoids uncomfortable prospecting, that's a sales problem. When a sales leader allows it to continue year after year, that's a leadership problem.

When a salesperson stops asking better questions, that's a skill problem. When leadership knows it and doesn't coach it, that's a culture problem.

When a salesperson stops developing relationships throughout an account, that's an opportunity problem. When leadership doesn't make relationship depth part of the company's growth strategy, that's a strategic problem.

If prospecting becomes inconsistent, the pipeline eventually becomes inconsistent.

If the pipeline becomes inconsistent, forecasting becomes harder.

If forecasting becomes harder, growth becomes less predictable.

If new business slows down, the company becomes increasingly dependent upon its existing book.

If salespeople aren't developing deeper relationships throughout their accounts, they become vulnerable.

If they're only connected to one or two people, they don't really have account depth.

If they're not having meaningful business conversations, they don't discover new needs.

If they're not creating meaningful value beyond the existing product or service, they become easier to replace.

Relationships become one of the most precious assets in enabling and future-proofing business growth.

Client relationships aren't simply a sales asset, they're a company asset.

CEOs, Inspect What To Expect

This isn't about nor doesn't mean micromanagement, it means leadership.

Great sales leaders don't simply ask... How are you doing against your quota?

They ask...

• How are you developing?

• Who are you building relationships with?

• What are you learning?

• Where are you uncomfortable?

• Which accounts are you penetrating?

• What meaningful business conversations are you having?

• What are your clients telling you?

• What are you doing differently this quarter?

• Where are you stuck?

Possibly, the most important question... What are you doing today that you weren't doing a year ago?

If the answer is not much, that's not a salesperson problem you should ignore, that's a leadership conversation you need to have.

Rocking The Boat Is Exactly What You Need To Do

Leadership may sometimes avoid difficult conversations because they fear disruption.

Avoiding the conversation doesn't eliminate the problem, it simply allows the problem to compound.

• You may preserve short-term harmony while sacrificing long-term growth

• You may avoid upsetting one salesperson while frustrating the rest of the team

• You may protect a legacy relationship while allowing your organization to become increasingly dependent upon yesterday's success

• You may avoid discomfort today and pay for it in revenue tomorrow

This isn't leadership, this is postponement.

Sometimes the most caring thing a leader can do is have the uncomfortable conversation.

Not from anger, ego or punishment, but from belief... I believe you're capable of more.

Your Mirror Moment

I'd encourage you to take a hard look inside your sales organization.

Not just at the numbers, look underneath the numbers.

Ask yourself...

• Where have I confused tenure with performance?

• Where have I confused relationships with relationship depth?

• Where have I confused activity with meaningful activity?

• Where have I accepted good enough because challenging it feels uncomfortable?

• Where am I allowing yesterday's success to justify today's lack of growth?

• Who on our team needs more coaching and who have we stopped challenging because it's easier that way?

This might be the hardest question... Have I, as a leader, been fostering the very complacency I'm complaining about?

Growth Requires Discomfort

Your salespeople are the corporate athletes of the business world.

You must instill the environment where...

• Practice is the norm and the standard

• Preparation is done by all

• Everyone studies their clients

• Everyone asks better questions

• Everyone develops authentic relationships, meaningful value, inspirational experiences, and disciplined habits

• Everyone prospects consistently

Why? Because...

• The market changes

• Your clients change

• Technology changes

• Expectations change

A sales team full of sales professionals aren't necessarily the people with the longest resumes, they're the people who remain curious enough to keep growing.

CEOs and Presidents, Here's My Challenge

Starting today, right now... Don't start by telling your salespeople they need to change, start by asking what you need to change.

• Where have you tolerated complacency?

• Where have you stopped challenging people?

• Where have you allowed seniority to become an excuse?

• Where have you accepted that's just how they are?

• Where have you prioritized avoiding conflict over creating accountability?

• Where has comfort replaced curiosity?

• Where have you allowed the sales culture to become comfortable when the marketplace certainly isn't?

And finally... What would happen if you raised the standard?

By this I mean not through fear, but through belief. Not through pressure, but through purpose. Not through empty accountability, but through genuine development. Not by demanding people work harder, but by helping them become better.

The goal is to build a sales organization that can consistently create trust, meaningful value, exceptional client experiences, deeper relationships, new opportunities, and sustainable revenue growth.

It may require you to rock the boat, but perhaps the boat needs rocking. Perhaps it's been sitting too comfortably in the sales harbor for far too long.

Growth only happens when leaders are willing to tell the truth, challenge the status quo, develop their people, protect the customer relationship, and create an environment where continuous improvement isn't a slogan.

I'll leave you with the question I started with... Why are you allowing this to happen?

An even more uncomfortable question... What if the person who needs to change first isn't sitting in the sales department?

When leadership gets comfortable, the organization eventually learns to be comfortable too.

Comfortable organizations don't create extraordinary growth, they protect what they already have, until someone else comes along and takes it, and we all know who that is, don't we?

Originally published on Larry Levine's LinkedIn.