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Upskilling and the war for talent

We used to call education the four and 40. Go to school for four years, work for 40. What’s now is you are going to have to learn some sort of new skill every four years.

I was listening to a great episode of Masters of Scale (Rapid Response) this week with guest Rachel Carlson,  co-founder and CEO of Guild Education.

She shared “100 million Americans, over two-thirds of the workforce today in America, need re-skilling or upskilling in the next decade in order to be relevant, employable, and be able to survive in the economy of the next decade. The problem is those folks don’t know how to find what school or program they ought to go back to, let alone what they ought to study.”

“So the half-life of a skill is now about four years. So if you’re learning anything skills-based, you are probably getting about four years worth. And so the future of work, the skills are going to evolve, right?

“We call that the four and 40, right? Go to school for four years, work for 40. The four and 40 is dead. So dead. What’s now is the every four. You’re going to have to learn some sort of new skill every four years. Now, I don’t know exactly who your listeners are, but if they’re like you and me, Bob, we’re probably some of the edge cases. You and I will learn the new Slack. And if somebody ever changes and builds the next Excel, we’ll learn the next Excel. But for the vast, vast majority of Americans, literally more than two thirds, they’re going to be wholesale learning new technology every four years. And that’s the reality that we’re not totally reckoning with right now.”

We are entering a new pandemic / post pandemic (depending where you live) economy. Everything will be different.

How will you prepare for your future?

What do you need to accept to be ready?

Defeating Average.


Are you an imposter?

I think we all are at some point. This discussion has been coming up more and more recently.

Are you handling the pandemic ok? Yes, I mean nooo!

How are you handling the scope of your new role? Great, I mean, ugg flailing!

You seem to be onboarding your new team well and meeting customer expectations. Yes, I am! Noooo, I am struggling to keep up!

Does this sound like you at all?

We all have a lot on our plate right now and may feel like an imposter balancing our job, our pandemic life, and our family.

It’s ok to say, woe, it’s a lot right now and sometimes I am on the struggle bus.

People appreciate honesty.

Personally, some days I feel like I have it nailed and the next day, I don’t at all!

What is important during these times?

  • Be gentle with yourself, it’s ok to admit…even to others.
  • Partner with other people who can help you get over the hump.
  • Remember each day is a new day and with good sleep, you will wake up refreshed and be able to begin again.

If you are not struggling right now, it’s possible you are not being honest with yourself.


Defeating the struggle together!



Are you anticipating where the puck is going?

“Skate to where the puck is going, not to where it has been.”

I was watching Master Class last week and they have a new series with Wayne Gretzky. I was fortunate, I grew up where he played the first decade of his career in Edmonton. He is one of hockey’s greatest players, if not the greatest, depending on your view.

When asked why he was so good at the game of hockey, he famously said: “I skated to where the puck was going, not to where it had been.”

He was talking about anticipation. Perhaps his greatest asset. People used to say he had eyes in the back of his head. 

In an episode in Master Class which I highly recommend (for hockey fans this series is worth the cost alone!), he talks about how his father Walter was ahead of his time in thinking about the game.

“I remember I was watching hockey on Saturday nights and my dad would say, I want you to watch the play, and draw where the puck is going all period, but don’t look down at your paper. You need to be able to see the play and have your head up. I would then analyze where the puck had been and it was surprising. I kept doing this over and over again until it transferred onto the ice.”

Anticipation. One of Gretzky’s greatest assets.

How are you anticipating where the puck is going in your life? Are you putting in the work to be world-class?

Defeating Average.


Are you languishing AND flailing?

I was listening to a great podcast from Dr Michael Gervais on Finding Mastery and he had a great guest Dr. Katie Milkman, who’s a behavioral scientist, and wrote a book recently with her focus “that optimism comes when you have a fresh start”. 

Maybe it’s from a life event, or for something you’re striving for. Maybe it comes from pain, or you’re sick and tired of being sick and tired. It can come at any time, it can be from different chapters in your life.  It can be after a rough quarter, a challenging month, a surprising week, and or sometimes daily focus.  I like to think I have fresh starts of some sort on a daily basis. 

Optimism, even if you’re not always optimistic, we all have that ability to find it.  It can be that pivot point or that first timely start. I encourage you to think about that, think about the science, and be on the lookout for the opportunity. 

Sometimes when you’re looking for it you find it or when you’re not looking for it.

Highly recommend the episode.

Defeating average with optimism.


Does your boat size fit the task at hand?

I was sitting up on the patio of our building in New York City looking at the boats going by. We are down in Battery Park which is just next to Tribeca. You can see the Statue of Liberty off in the distance and it’s amazing how many different types of boats go through the Hudson. 

In our new program at Salesforce, building out a Sales leader coaching practice, one of the things we have been talking about is you to best utilize your resources when working with a customer.

I see similarities between the size of the boat you move in and how you bring value to a customer.

Sometimes you are paddling in a two-person kayak.

Other times you may need a little bit more horsepower and have 4-6 people in a speedboat.

Sometimes and a little more rarely you see these pretty big yachts that are coming in from the islands and they are parked down by this little harbor and we walk down and check them out.

Kayak is like your account executive and solutions engineer going to help a customer who just wants to get up on one product.

The speedboat you’ve got a few more resources in there with, maybe it’s the account executive, one of your co-Prime’s it’s your Solution engineer, maybe it’s someone from the Business value team working on a Total cost of ownership analysis, and it’s focused on that midsize industry deal. 

And then there is the yacht. That’s the full power of your company.  At Salesforce, we like to provide value by holding executive briefings for our customers on key topics they care about, we host fun and creative marketing events, and we invite other customers to share how they are succeeding with Salesforce. We host really big industry events that bring the whole ecosystem together like Dreamforce (in person or virtually last year where millions of people came together).

We are a sales-focused organization and everyone helps lean in to win as a team. With 60K employees, you can think about everyone as stars in the sky that can be pulled down to join the conversation on the big boat and share some expertise that solves a challenge a customer is focused on.

It doesn’t matter what size of company or industry you are in, these three different approaches are available to you in some form.


Defeating Average as a team.



Are you outnumbered against fear?

“If you face just one opponent, and you doubt yourself, you’re out-numbered.” – Dan Millman

We all have fear. Fear of failure, fear of not being enough, fear of other people’s opinions, fear of covid.

In his book Way of the Peaceful Warrior, Dan Millman talks about doubt and fear, it’s an awesome read.

After recently reading more on the fear of fear itself, I found myself preparing for a recent presentation realizing I was not being fearful of not presenting well…I was fearful of fear itself. Trippy right.

Once we realize that fear is a part of being able to perform and it will always be there, you can notice it, like a cloud passing, name it and move on.

We can all face one opponent. If we can harness and leverage fear, we will be less likely to be outnumbered. In fact, if you can talk openly about your fear with others, you can outnumber fear.

Defeating Average.


My Nutrition was out of wack

I have been trying to get back into shape. I am getting in a good amount of outside time, riding the peloton a couple of times and a week, and slowly easing back into running.

It really hit me after a run 6 weeks ago and I felt completely out of shape when I was done. 

Is this it, I was thinking? Maybe the good running days are done.

I called a friend who has been accelerating in his 50+ year age for some advice.

He said:

  1. Stretching and a lot of it
  2. Nutrition – Are you being honest with yourself?
  3. East back into it


I have been on a stretching binge, my wife can attest to it. Lying on the floor all over the apartment. What has really helped is focusing on it with my trainer. Instead of stretching for time, stretching for deep breaths (that are a similar amount of time). I can report making big strides in my standing stretch and things are progressing.


I started following a program with my friend and nutritionist Dr. Marc Bubbs. I needed an accountability partner, and a stronger why.

Feeling old and slow was enough to get me kick-started.

A key piece of this has been sharing my nutrition goals with my wife and without her assistance in making some amazing and delicious meals and would not be making the progress I want to be.

Finally, easing back into it.

It’s an ultra-marathon, not a sprint. I want to feel healthier, lighter, more flexible for myself and my family, and am on my way there.

Anyone else who needs an accountability partner or support, reach out!

Defeating Average as we age.


Are you communicating ahead?

Coming off a company QBR (Quarterly business review) this week, three key learning themes came out.


Growth mindset

  • Are you open to new ideas and new ways of doing things?
  • In these covid times, we need to be willing to throw things out that no longer work and find new ways that do


Beginner’s mind

  • Blank slate thinking. New problems require new solutions and as Brene Brown reminded me in a podcast recently, spend 55 minutes of the hour getting clear on the problem and spend 5 minutes on the solution



  • When you work for or with a matrixed organization, alignment is key.
  • Over Communicating never hurts, and making sure your audience understands your intention by hearing back in their words
  • Meeting people who are key stakeholders to executing on your project on a regular basis in the spirit of partnership


To Defeating information overload and landing your message.



You’re Not Listening

I was listening to a great podcast this week from Preet Bharara where he interviewed Chief CNN Correspondent Clarissa Ward.

They discussed what makes a good journalist, a good lawyer, and a good parent. Clarissa Ward has been embedded in a lot of war zones. 

“We do a lot of talking in our society. We don’t do enough listening, and the one piece of advice that I would want to give to my young boys she said, is to do more listening than talking.”

 Preet said the same thing. “If you want to be a good lawyer,  be a good talker. If you want to be a great lawyer. Be a good listener.” 

I think we can all take that piece of advice in whatever profession we reside.

The more we can pause the more we can stay curious, the more we can listen to another person’s point of view.

Defeating Average.


The best way to stay in shape is to not get out of shape

“The best way to stay in shape is to not get out of shape.”

– Kelvin Beachum, Offensive Tackle, Arizona Cardinals

I had the good fortune of being on a customer panel with Kelvin last year and we caught up recently. Training camp in the NFL starts shortly and he focuses on staying in shape all year long.

When he spoke I recall him sharing a few things related to health, nutrition, and mindset. This is a summary in my words.


  • I stay in shape all year long. To compete at the NFL level it’s what I have to do.
  • I have dinner with the family and then we start to wind down around 830pm. Sleep is critical for my success.
  • More energy = More Success


  • I pretty much eat the same type of meals every day based on my nutritionist. It takes the thinking out of it and it’s easy to stick to.
  • Consistency + less decisions = Prioritizing what’s important


  • I get up at 430am every morning and well ahead of my wife and kids to get everything I need to get done.
  • I do a lot of work in my community and leverage my platform to help pay it forward. 
  • Front loading the day + gratitude  = Turning the flywheel

Defeating Average.