Most productivity advice (especially on morning routines) is totally UNREALISTIC.
No one has time for an hour-long morning routine that takes 21 steps. Especially if you have kids.
Here's how I have my best week every week:
✅ Do something hard and physical first thing Monday morning
Monday morning sets the tone for the rest of the week. Make it hard to not have a killer week.
For me, it's scheduling an Orangetheory workout first thing Monday morning.
The mental win of doing something hard to get the week started is a game changer for me.
For you, it could be a workout at the gym. A workout at home. A walk around your neighborhood. Don't overthink it. Do something physical, and keep it simple.
No excuses. Get after it.
✅ Plan to plan
I learned the best time management lesson of all time as a 19 year college freshman.
My VP of Sales taught me to:
- Take 20-30 min. every Monday to plan the week
- Take 5-10 min. at the end of every day to plan the next day
There's no secret to time management. This advice is absurdly simple. But it's about consistent execution.
The most important meetings to schedule every week are the meetings with yourself:
- Outbound time
- Meeting prep
- Personal development
- Fun stuff
- Family stuff
- Reflection time
- etc.
✅ Weekly feedback loops
Every Sunday for the last 7 years, my wife and I do what we call a "Sunday Retro."
I set a reminder on phone every Sunday. And it takes about 10 min. for us to talk about:
- Start: "What should we start doing that we're not?"
- Stop: "What's not going well that we should stop?"
- Continue: "What's going well that we should continue?"
If you don't have a spouse, schedule a Sunday Retro for yourself. Or do a version of this for your work.
Do NOT let more than a week go by without course correction.
This keeps you laser-focused on your goals.
~~~
What helps you make the most of every week?
Sales Managers: Don't expect your AEs to cold call if you don't know how to.
This kills me.
Every week, I meet with leaders asking their reps to do more pipegen. Make more calls. Send more emails.
But they never participate with the reps. And they couldn't do it themselves if their lives depended on it.
THIS DOESN'T WORK.
You can't ask your reps to do what you are unwilling or able to do yourself.
If your team is struggling to build pipeline right now, get back to the basics.
→ Do our managers know how to outbound?
→ Do our managers know what good outbound looks and sounds like?
→ Do our managers do outbound with their reps?
→ Do our managers set weekly outbound goals with their reps?
→ Do our managers reverse-engineer the sales math behind every rep's sales goal?
→ Do our managers provide weekly outbound coaching to their reps?
→ Do you, the senior leader, talk to your managers about outbound?
→ Do you, the senior leader, talk about outbound in your all-hands calls?
→ Do you, the senior leader, give public shouts to reps doing well at outbound?
~~~
My friend Garrett Grastion was the top sales manager at Zoom in 2023.
Know what he does every Friday morning? A prospecting power hour with his entire team. And yes, he prospects too during that time.
Don't expect your team to do what your front-line leaders are unwilling or unable to do.
Who's with me here?
Enterprise meetings REQUIRE enterprise effort.
If you want to:
- Land meetings with enterprise execs
- Move your org up-market into bigger enterprise deals
You don't deserve the meeting unless you invest enterprise effort.
Sending "personalized" cold emails isn't good enough.
Pointing out something from a quarterly report isn't good enough.
You need to make an org-wide investment in building tools and processes for reps to deliver REAL value to prospects.
Here are three examples:
✅ Experience the brand
If you sell to consumer brands, go experience the brand. Be a customer.
Example: If Patagonia is one of your accounts, go into a Patagonia store. Go to the website. Load up the court. Buy something.
Show the exec you experienced the brand.
✅ Show a problem
If you can fix a visible problem, expose it.
Example: Run a website audit. Run a digital experience audit. Call into their customer support line.
Show the exec their problem and the impact of that problem
✅ Share tailored insights
Share something educational that's tailored to the prospect's business.
Example: Run a competitor assessment, secret shop their competitors, run a risk assessment
~~~
This is not only the future of outbound—it's becoming the only way to land an enterprise meeting.
This requires deliberate collaboration between marketing and sales.
If you want enterprise meetings—they REQUIRE enterprise effort.
Agree or disagree?
Feeling burned out? In a slump?
I caught up with a rep and friend last week. He's in a slump.
Things aren't going his way. He's feeling uninspired, etc.
I've never met a top rep, senior exec, or a successful business owner this doesn't happen to.
These are two simple tips that I gave this rep. And that I follow myself.
👇
✅ Create consistency and discipline OUTSIDE of work
Please, do not wrap up your entire identity and self-worth in your work. You are more than what you do.
I've been there—it's not worth it. I sacrificed my mental & physical health for...what? People I don't respect nor have a relationship with anymore.
The sales roller coaster is unavoidable. If your self-esteem is tied to work, you're gonna feel like sh*t.
Find areas outside of work to create consistency, discipline—and ultimately: pride.
For me, it's exercise. I take a lot of pride in staying consistent with 3-4x per week at Orange Theory. And playing basketball a few times per week.
Find your thing to be consistent with outside of sales.
✅ Make friends with peers
I didn't understand the importance of this until I met Jeff Bajorek back in 2018.
When we met, I asked: "Do you have this problem where you don't know anyone who does what we do?"
His response: "No, actually I don't. Let me introduce you to some folks."
Since then, I've made my best friends through work. I lean on my friends for accountability, inspiration, and feeling seen/heard.
You need to know more of your peers. Especially the ones outside of your sales org.
Make a point of meeting someone new every week.
~~~
How do you prevent or deal with burnout and slumps?
Call me crazy—but a good sales cycle has both phone calls and virtual calls.
From a relationship building standpoint, I can accomplish in 10-15 min. over the phone what could take multiple virtual calls.
I was texting back and forth last week with a current client. We're putting together a second phase of training for their enterprise AEs.
And price came up.
"How much will it cost to..."
"What will happen if..."
"That won't make sense to..."
So what did I do? I picked up the phone.
We talked for about 10 minutes:
- 2 min. on pricing
- 8+ min. shooting the sh*t
I build way more rapport over the phone. It's more real when you talk to someone walking around their house, grocery shopping, driving, etc.
Here are a few ways to take action on this:
✅ Texting back and forth with a prospect or client? Pick up the phone.
✅ Prospect responds to a cold email? Pick up the phone.
✅ Have a quick question to prep for an upcoming group call? Pick up the phone and call your champion.
✅ Not sure how that sales call just went? Pick up the phone and call your champion.
When in doubt, #pickupthephone.
If they don't answer, shoot them a text asking for a few min. to catch up.
Sometimes it pays to do things the old-fashioned way.
Agree or disagree?
3 sales calls canceled same day on me last Thursday.
My thinking?
You can whine about it. Or you can do something about it.
What's important is how you maximize the time you get back.
Here's what I did:
✅ Re-engaged with three old clients
I found three clients I haven't spoken with in months. Sent them texts to connect and landed a meeting to talk about another training engagement.
✅ Reached out to prospects engaging with me
I ran a quick Sales Nav filter of every prospect engaging with me, visiting my profile, etc.
Found three great prospects and sent them emails & LI messages.
You can do something similar in your sales engagement tool. Who's opened your emails in the last hour?
✅ De-risked a deal
I opened up HubSpot and looked at a few late-stage deals that didn't feel solid.
Called my champions. Had one quick convo about a risk I wasn't aware of in the deal. Set some time to talk more about it.
~~~
You need a list of activities to maximize 30 min. blocks that show up unexpectedly in your calendar.
It's the "get sh*t done" mindset and no matter what, today will be productive.
How do you maximize the time you get back when calls cancel?