Hey, 👋 Scott from The Sales Mastermind here.

Today’s edition only takes 4 minutes.

Being a manager is simple, but not easy.

It’s about expectations, support, and accountability.

Today we’ll cover:

• Storytime
• Chaos
• Expectations

Storytime

I currently coach two first-time sales managers. 

Both are/were excellent sellers who became “managers”.

One is a founder who was the only seller in a ~15-person agency. And, for now, he will continue to sell as founder-player-coach.

The other was the business’s top seller and was promoted to a player-coach management role in 2025. Then, recently, he was again promoted to full-time manager of a team of 7, which is rapidly expanding to 10-15 or more, this year.

Despite both coachees being in different businesses and industries, and being vastly different individuals, they face the same first-time-manager problem:

Chaotic process, meaning no single action or activity, or even a combination of activities, will result in a sale.

And that every seller wants to do it their own way. Especially experienced sellers who were the manager’s pre-promotion peers only 1-3-12 months ago.

For both of these new managers, we are working through roughly the same process to set and enforce expectations for their teams.

Ultimately, the only way to lead a sales team is to:

• Set the expectation
• Document the expectation
• Train the team on the expectation, and
• Hold the team accountable to the expectation

Then get out of the way.

Chaos

Sales is a chaotic system because, from closing deals to generating pipeline and everything in between, no single action, activity, or combination of activities will result in the desired outcome.

The chaotic nature of sales is why cold outreach can be so demoralising. If you make 100 dials today, you may have zero conversations. But then you make 10 dials tomorrow and book 4 meetings.

Therefore, a sales manager’s job is to set expectations for the team. Starting with the end in mind and working backwards.

Set the Expectation

Management begins by defining success. And it starts with the outcome, works back to the input, and ends with behaviours.

So start by defining a single, measurable outcome. For example:

• Revenue closed won
• Number of deals closed won
• A ratio, for example, “interested buyers” to “closed won deals”

You also need to define when a deal is considered closed - common examples are when a buyer signs an agreement or when a certain percentage (100% or 50% are common) of the payment is collected.

Next, a manager needs to set expectations for how the team will build their pipeline. For example:

• The number of self-sourced meetings per week
• The number of activities per week
• A minimum speed-to-inbound-lead time

Lastly, a manager needs to create expectations of behaviour. Some examples include:

• Is there a set time for the team to be in the office/online?
• When a seller has a question, to whom do they ask and how (by phone, Slack, text, etc.)?
• What is considered Closed Won, and when does the seller need to get back involved after a deal is Closed Won?

Document the Expectation

Next, it’s time to document the expectation. When written down, it can be referred to and enforced.

I call this document a Playbook; one of the managers mentioned in Storytime calls theirs a “Closer’s Handbook”.

Here is a template I’ve shared with other sales teams as a starting point.

Remember, every company has a very different playbook as each buyer, product, and business is inherently different.

Additionally, the best playbooks have absolute clarity for the definition of each stage of your CRM pipeline. That way, it’s clear how “Proposal Sent” differs from “Final Negotiation”.

Without these definitions, I guarantee your team will be using the CRM in wildly different ways. And it’ll be painful to support your sellers effectively.

Train the expectation

Now that you’ve written it down, it’s time to train your team.

Training is either drip-fed - a session and focus once/twice a week until done.

Or you can run a 1-2 day team-wide meeting and get through it all at once.

Neither is inherently better; they’re simply different styles of change management.

When you train your team, it is vital to add questions or enforcement mechanisms throughout the document to ensure the team is paying attention and doing any pre- and post-reading.

Two examples of this are adding, semi-randomly, statements like:

• “If you made it this far, send me an email with the subject Purple Monkey, and you’ll get a coffee voucher”
• “Once you finish this section, email me the name of our third pipeline stage and why it is overused”

Hold the team Accountable

Lastly, and this is by far the hardest, your job is to hold the team accountable to the expectation.

Many sellers will be resistant to any changes, and even new sellers will sometimes resist being “told what to do”. Especially those sellers who want to do it “their own way”.

So focus on the original expectations and how they cascade down.

If a seller is meeting or exceeding the single, measurable outcome, that means success - get out of their way. Let them sell.

However, if not look at your pipeline building expectation, there are two paths:

• The seller is doing everything you asked of them - therefore, your job is to provide additional training, support, and help them achieve success.
• The seller is NOT meeting their pipeline-building expectations - they have a choice to either start doing the work or (eventually) leave the company.

The final part of holding your team to account is how well each seller aligns with the behaviours you expect.

Ultimately, we want everyone to honour every behaviour, but this needs to be balanced with their personality and everything else in their lives. Use your judgement.

Remember, Caesar’s wife must be above reproach

Lastly, whatever you expect, make sure you live the behaviours and the expectations at least as much as you expect your team to.

Management is simple: create, document, train, and enforce clear expectations.

Until next week,
Scott Cowley

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