Jennifer Bleam

10/09/2026

“If I follow up too much, I’m afraid I’m going to annoy my prospect.”

This fear causes a lot of people to give up on good leads too early.

Your prospects are busy!

They miss emails.
They forget to respond.
Their manager goes on vacation.

Silence doesn't automatically mean a prospect isn't interested.

In fact, research suggests it takes around eight touches just to get a first meeting with a new prospect.

So if you followed up once or twice and heard nothing, that is not a clear “no”.

BUT…

That does not mean you should keep leaving voicemails that basically say, "Just following up to see if you're ready to buy yet."

That’s obnoxious and gets old really fast!

Good follow-up should add something of value to the relationship.

A useful anecdote
An article or blog post that’s pertinent to the problem they need solved
Something that (genuinely) made you think of them

You don’t need to follow up forever.

But you also can’t give up after two attempts.

Go look at your pipeline.

How many people are sitting there right now that YOU decided weren’t interested… when the reality is: you just got tired of following up.

10/08/2026

There’s a point in every sales conversation where you have to ask yourself a question most people avoid...

Is this prospect actually worth pursuing?

I’ve seen salespeople spend weeks (or even months) trying to close a deal that was never going to close.

They keep pushing because they’ve already invested so much time, energy, and emotion into the opportunity.

It’s the epitome of sunk cost fallacy.

But sometimes the smartest sales move isn’t following up “until they buy or die”.

It’s walking away.

The key is looking at the actions of the prospect.

If they’re a great fit…
If they TRULY want and need your service…
If they were engaged recently (but went dark for a short amount of time)...

Then patience can make sense.
Pursue them.

But remember:
Budgets change.
Timing changes.
Decision-makers get busy (or leave the company).

The question isn’t whether the sales process has gotten difficult.
The question is whether there’s real evidence that the opportunity is still alive.

Are they responding?
Are they taking agreed-upon next steps?
Is the problem still a high priority?
Is there still budget? Urgency? A path to a decision?

Because there’s a big difference between a deal that’s just taking longer to close than you expected…

And a deal you’ve got on artificial life support because you can’t admit it’s dead.

You will NEVER close every prospect.

There’s a difference between persistence and wasted time, energy, and effort.

Sometimes the smartest thing you can do is close the file, redirect your attention, and go find a new prospect who actually wants to buy.

It doesn’t always feel great.

But that’s part of selling.

10/07/2026

Over the past year, I’ve talked to hundreds of MSPs about AI.

Some are way out in front. Others are experimenting. Many are still trying to figure out what they should even be saying to clients.

And one thing has become really clear:

Knowing a lot about AI does not automatically mean you’re ready to make money from it.

You can use ChatGPT every day. You can test agents. You can watch every demo, attend every webinar, and know more about AI than most of your clients.

But if you’re still waiting for clients to bring AI up, you’re probably not as far along as you think.

I’ve started looking at it in 5 levels:

Level 1: Waiting
You answer AI questions when they come up, but you’re not creating the conversation.

Level 2: Talking
You’re starting to bring AI into client conversations and sharing examples.

Level 3: Discovering
You know how to uncover real business problems AI could help solve.

Level 4: Monetizing
You have a repeatable way to turn those conversations into paid discovery, projects, and revenue.

Level 5: Leading
Your clients come to you before they make AI decisions. You help them figure out what makes sense, what doesn’t, and what to do next.

That’s the level I want MSPs working toward.

Not becoming AI developers.

Not building everything themselves.

Becoming the person the client calls first when AI comes up.

Where would you put yourself today?

10/06/2026

“People buy from people they like.”

Chances are, you’ve heard this phrase a million times in your life.

And it’s 100% true.

But, as with many things in life and business, there’s nuance here.

Your prospect probably won’t buy from you if they don’t like you.

But that doesn’t mean you should become soft, conflict-averse, and overly accommodating.

You have to be able to ask tough questions, push back against patterns & habits that aren’t serving your prospect, and follow up (even if you feel like a pain).

You must follow your sales process, stand your ground, and insist that your prospect adopts your security stack.

You need to close, get a firm next step, and defuse objections.

Don’t mistake “being liked” for “being mamby-pamby”.

There’s a pendulum here, and I see FAR too many salespeople wanting to be liked… at the expense of their close rate.

If you wonder if this is you, drop your latest sales transcript into AI and prompt, “Where did I avoid a tough question or allow the prospect to take control because I wanted the prospect to like me or feel comfortable with me?”

I bet you’ll be surprised at the results!

10/02/2026

The urgent stuff almost always wins.

Which is why "tracking your numbers" often gets neglected.

Thankfully, AI can change that.
Details in the video...

09/30/2026

09/29/2026

Feeling behind on AI? You don’t need to learn everything.

Here's a proven fundamental to help you learn a lot of information... in a short amount of time.

And how to pair that tried & true tactic with today's tech.

09/28/2026

If your AI sales conversations keep turning into free consulting sessions, there’s a good chance you skipped a step.

In my CLOSE AI Sales Method™, that’s the L: Lead step.

You should be guiding the conversation, setting the agenda, and keeping the buyer focused on outcomes.

If you don’t lead, the conversation gets hijacked by tools, random questions, and “what if” scenarios.

09/25/2026

Every business has a list.

The things you want to do or should do.
The things that would probably make the business better.

But there’s never enough time, staff, or bandwidth.

Maybe it’s following up more consistently with old leads.
Cleaning up the CRM.
Documenting processes.
Checking in with clients more consistently.

This is one of the AI opportunities that businesses are overlooking.

Of course, AI can help you do existing work faster.

But it can also give you the capacity to finally check some things off the wish list.

If I was talking to a client about AI right now, I’d ask about their “someday list”.

“What have you wanted to do forever, but never had the bandwidth to make it happen?”

Because finally getting to do something you’ve talked about (and hoped for) for years feels GOOD.

And if AI makes it possible, that’s a much more powerful sale than “we can save you a few hours each week.”

09/24/2026

No matter what you're selling, business impact is crucial.