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How to Stop Drowning and Start Systematizing

I couldn’t breathe.

Every time I kicked hard to get a gulp of air, I lost a little strength. The riptide pulled me out further. I sunk below the waves.

I was pulled out of the ocean in Hawaii, glad to be alive.

But then I returned home – to the office – and felt the same feeling.

Drowning. Firefighting. I couldn’t get ahead.

But this time, no lifeguard on a jet ski to pull me out of the riptide.

There was one big difference though. And that is that I had created the ocean of work that was drowning me. After all, I was the CEO. The choppy waters, the endless riptide pulling me was my own doing.

Since then I’ve talked to hundreds of entrepreneurs, and most feel the same.

Here’s how I work with clients and portfolio companies to build a raft, then a rowboat … and then, a battleship.

Step 1: Map The Business Functions

First, I zoom out and look at the business from a high level. Break it down into core functional areas like sales, fulfillment, marketing, HR, accounting … Make a comprehensive list of every function the your company, even if some of those roles are currently being done by the same person (i.e. the founder).

This exercise exposes just how intricate the business is and how vital it is to have standardized systems across each area. Like a clock, if one gear is off, the whole mechanism grinds to a halt.

Step 2: Define All The Tasks

Now I drill down into each function. Identify every repeatable task that role performs, whether it’s sending invoices, onboarding new hires, or creating social media content. Get granular. The more tactical we can be in defining each discrete step, the better the documentation will be.

Note how frequently each task recurs. Is it a daily task like customer service? Weekly? Monthly? This will help you prioritize which tasks are ripe for systemization first.

Step 3: Assign Owners

Next, I designate who is responsible for managing each task. Tasks can’t fall through the cracks if someone’s name is next to it.

This owner may be the entrepreneur initially, but the goal is to eventually delegate tasks so he’s not the bottleneck. As you systemize and document how each one is done, they get delegated.

Step 4: Document Processes

Now comes the documentation piece. For each task, I have the task owner map out how it’s done from start to finish. What are the exact steps? What inputs do they need to complete it? This is writing the owner’s manual for each task.

I like having them record themselves doing it and create a checklist from that.

Step 5: Streamline with Technology

Once everything is documented, I take a second pass to identify opportunities to leverage technology. Could any manual tasks be automated with software or AI?

Even simple changes like using templates or project management tools can be big levers.

Step 6: Centralize Knowledge

Finally, I collect everything in a master playbook that’s accessible to everyone. This living document becomes the single source of truth for how everything gets done in the business.

As we refine processes, swap owners, or incorporate new tech, the playbook evolves. But everyone is always working off the same updated protocols. No more misalignment.

Building your life raft is a process. You just need to stop thrashing for long enough to realize your predicament … And swim out of the riptide.

Want a cheat sheet to growing a thriving business? Get business training for free at the CEO Workbench.

October 4, 2023

Innovate Or Die. You Have 3 Years.

My friend John’s business is dead. He just doesn’t know it.

He runs an agency that’s headed straight for irrelevance as AI tools improve month over month.

Growth was decent in the past years. But now it’s stalled.

Should he double down and tweak the existing model? Or is it time for something completely new? New offer? New product? New business?

His dilemma will be yours sooner than you think.

And it could determine whether your business survives the next decade.

When 20% Growth Goes Missing, It’s Time to Innovate

In the early days of your business, growth was easier. You figured out to go from nothing – to something. But lately, you’re justifying that “things are fine” when revenue creeps up 5%.

“If I can just increase 5-10% per year that’s great”

No, it’s not.

That’s a warning sign of irrelevance.

It means you’ve tapped out your existing market or existing offer. Things have shifted around you.

Is your current business model is doomed? Maybe, maybe not. But the writing is on the wall that it needs a serious revision.

You may be able to revive growth by making tweaks, like:

Embracing new technology to enable delivery
Moving upmarket and targeting bigger customers
Tapping into an adjacent niche you’ve ignored until now
Optimizing your sales and marketing process

But incremental fixes may only buy you time. To thrive instead of wither, you may need to shake it up more:

Will Your Model Survive the Future?

Let’s do a thought experiment. Fast forward 5-10 years into the future. Will your current business model still work?

I did this with John, now let’s do this together. Here are some big picture trends to consider:

How customers buy is changing. More buying happens online. Buying cycles are faster. Loyalty is fragile as customers try new options. Are you keeping pace? Are you giving customers reasons to try you for the first time? To stick with you?
New competitors are emerging. Low cost SaaS tools can replace entire services businesses. AI is automating complex tasks. New competitors with novel models will keep coming. How defensible is your niche? Your delivery model? Are you working to disrupt yourself before someone else does it?
Customer needs are evolving. With more options than ever, customers demand superior experiences. They expect transparency and alignment with their values. Are you exceeding these rising expectations?

Be brutally honest with yourself. If your current model stays unchanged, will it survive these changes?

Beware the Risks of Building Something New

Revolutionizing your model with big moves sure sounds appealing. Hey, we’re founders and “entrepreneurial ADD” is part of what got us here.

No doubt the idea of a fresh start and faster growth sounds appealing.

John and I have talked about this often over the years- should he start something else in parallel? Even before the existential threat this was an idea.

But … the grass is always greener. But don’t underestimate the risks and challenges:

Proving demand again – you’re back at square one trying to find product-market fit. You did it once with your existing business – but might not realize how rare that is. Not impossible – but it’s actually really hard.
New competition – competing with others who are further ahead in the new space. You’ve got a whole new set of competitors. Some of us love the fight (I’m guilty as charged) – but be prepared to learn a whole new landscape. It’ll be fun. But complacency isn’t an option.
Sunk costs – shelving existing assets that have taken time and money to build. Kill your darlings. You may think you’ve got a great process that delivers for customers. Fantastic. It won’t work tomorrow. Decide: rest on your laurels and risk irrelevance, or throw away work you did because it won’t serve you tomorrow.
Morale – employees may resist abandoning the model they know. You’re the leader, and leading through change is hard. You might need to look for some new team members who can look to the future.
Focus divide – split attention between old and new can spread you thin. It’s hard to focus on more than one business model, but it’s the price of future proofing. Again, it’ll be work.
Cash burn – financing the new efforts until revenue catches up. Innovation isn’t free. You’ll spend time and money. You can view it as “insurance” for your future business. Do you want to go uninsured and save a little today? Or invest for tomorrow.

This isn’t to discourage you, it’s to make sure you’re going in with your eyes open. Future proofing isn’t free.

But it may be the one thing between your business and irrelevance.

I can’t tell you what to do. It’s your business. Put on your big girl pants and make a decision.

Get Back to Business Fundamentals

I walked through John this thinking model that will help:

Before choosing innovation or optimization, take a step back. Revisit the core of your business:

Where is the proven demand? Forget assumptions. Talk to real and potential customers about what they truly want and need. What gets them excited?
What value are you building? How does your product or service create value in customers’ lives? Are there new ways to expand that value? Other ways to serve it with technology?
What lights your fire? Which path gets you jazzed every morning – improving the existing or creating something new? You’ll need to put in serious focus, so dreading the journey will only make it harder.
Which builds the better asset? Will one business model ultimately be more valuable if you wanted to sell the business? Keep the big picture in mind: building an asset for yourself, not a job.

The right choice will become clear if you ask the right questions.

It helped John clarify and make a decision.

When in Doubt, Run Experiments

Still can’t decide if it’s time to tweak or reinvent? Here’s where we landed with John’s business: run experiments.

Come up with a few hypotheses about what could work.
Test demand for the new model before going all in.
Keep the existing business humming while you validate and build up the new.
Once the new shows more promise, gradually shift focus. Manage both models under one roof, or split into two companies.

Tests and small scale experiments reduce risk. They help you make decisions based on real market feedback.

Sure, it’s messier than choosing just one path. But it boosts the odds you’ll end up on the right track.

The future is scary only if you haven’t planned for it. This is your wake-up call. And I want to give you a worksheet and process for doing this in your business: The Innovate or Die worksheet. Get a copy at the CEO Workbench: ceoworkbench.com

September 4, 2023

How To Never Get Derailed From Growing Your Company

Here’s how I guarantee that I’m never derailed from growing my company – and how you can do the same.

Every week, I was getting pulled into a fire. Some customer problem, an employee issue, something. My company was going nowhere. The classic “working in the business, not on the business.”

It had to change.

How To Stop The Madness

That’s when I sat down and asked the most important question (which you’ll see the answer to today): “Why am I always getting derailed?”

I started fixing it by breaking down hitting my growth goals. In the most simplistic way possible, what has to happen to grow the company?

I need the RIGHT PLAN and I need to EXECUTE THE PLAN.

I needed the RIGHT PLAN because confidence makes all the difference. It seems dumb, but it’s true – if you haven’t bought into the plan, you’re not going to prioritize it. If I wasn’t convinced I was headed in the right direction, it would be easy to let it slip.

The key to a plan you’ve got confidence in is to take the goal and break it into concrete steps and success criteria. (I’ve written here on turning goals into plans – can come back and this read later)

The second – EXECUTE THE PLAN – sounds simple, but it’s actually the hard part.

What Not To Do

What I used to do is:

create a one-year plan
create quarterly plans
forget the quarterly plans once a crisis happened
beat myself up that I didn’t do anything, and go back to (1) above

It was a doom-loop that made me think that somehow I wasn’t capable of hitting my company targets. Everyone else was just better than me.

But that wasn’t true. The reality: I was missing key steps in execution. I talked with entrepreneurs I respected. People who built companies I was envious of. How did they stay on task?

The key: time-blocked accountability.

The Formula To Never Get Derailed

How does it work? I had the first part right:

create a one-year plan
create quarterly plans

But after that I wasn’t bringing it down to actually getting things done in the moment. The calendar is the key.

Every project for growing your company must be ON THE CALENDAR.

Here’s how:

create a one-year plan
create quarterly plan
quick monthly review where I am
every Monday commit to 3-5 tasks to move forward
book tasks on the calendar with specific times
have someone beat you up if you don’t do it

Why It Works

Let’s look at why this works:

First, you’re getting granular. This isn’t just an idea at the quarterly level which is easy to let slide. By bringing it down to the month, you have a pulse on where you are.
By blocking time on your calendar every week you reserve time
And someone watching you is the unlock

I’ve been doing this for years, and work fires never derail me. I make more progress in 90 days than I made in a year the old way.

In fact, it worked so well I built myself an app to do this – it even calendars progress so I can’t get off track. App plus a person holding me to my commits = gamechanger.

Use the process above to fast forward your growth. Just make sure not to forget the last step and have someone hold you accountable.

Get a weekly list of short, actionable steps to scale your company with simplicity in the Boardroom Bulletin™.

January 10, 2023

Entrepreneurs: 8 Keys to Scale Your Business Quickly

I’ve created over 753 strategic plans for entrepreneurs. At the core of each one are two things: Simplicity and Scale.

Here are eight things to cover in your strategic plan to grow with less complexity.

Before we jump in – it’s important to realize that the same things that make your business fun (and profitable) to run are the things that make it irresistible to buyers when you want to exit. So you’re getting a double benefit focusing on these 8 keys.

Here are the keys:

1. Margin

Make sure you know your margins and they’re healthy for your industry. Too many entrepreneurs put their head in the sand because numbers are scary. Here’s the hack: just ask your bookkeeper for a report. And read it. Seriously, the numbers are already done for you.

2. LTV

Know the lifetime value of a customer. If you don’t know what a customer is worth you’re flying blind. You can’t plan marketing, staffing, or growth. Know and grow this number.

3. Systems

All wealth comes from systems. A company is a machine that takes in capital, people, and resources and produces customers and profit. Without defined systems you don’t have a machine. You have a medieval workshop. Those suck to work in.

4. Optimization

Optimize your processes to deliver higher quality for less time and expense. Many businesses can increase profits significantly by just fixing poorly run processes – and use that cash to scale. You’ll need to – scaling with bad processes is a recipe for failure.

5. Delegation

Learn to delegate the right way. A company where the owner is necessary isn’t a business, it’s a job. Learning how to delegate in a way that’s a win for both you and your team is an invaluable skill.

6. Management

Manage your team with clear goals and accountability. That starts at the top. For consistent results make sure to use business scorecards to manage by numbers, not by emotion.

7. Hiring

Compromising on hiring because you just “need a body” will cost you in the long run. Hiring an A-Player will multiply your business. The wrong hire can set you back years (it happened to me).

8. Retention

A company scales by upgrading product, team, and customers. Keep the right people, and shed the rest.

The Scale Cycle

These eight factors are part of my Scale Cycle that helps entrepreneurs how to scale their business with simplicity. Start by picking the one that will have the biggest effect on your company, tackle it, then move on to the next. Then… Repeat. It seems simple, because it is.

Get a weekly list of short, actionable steps to scale your company with simplicity in the Boardroom Bulletin™.

December 27, 2022

A New Year: How To Always Nail Your Strategic Business Plan

The year is almost over, and you’re probably going to miss the goals you set in January. Most business owners are in the same boat – BUT a few crush their goals every year.

Here’s why your business goals aren’t working, and what you can do to fix them.

Ever make a New Year’s resolution that went nowhere? Afraid you’re about to do it again in a few days? Annual plans for most businesses are like those. A burst of high hopes and effort, fizzling by February, because – Life gets in the way.

You’re putting out fires, and back in your old habits. What happened? You’re back at work and at the end of each day you can barely remember what you got done.

You go home and your spouse asks how your day was- and you kind of don’t want to tell the truth. You’re sensing your team is thinking you don’t really have a plan, only ideas…

The Secret to Hitting Business Goals

It’s fun to set big goals for your business – but why can’t you actually hit them? Here are three key things from entrepreneurs who nail their goals:

1) A goal without a plan is a wish

2) It isn’t about the goal, it’s about the habits

3) Be accountable or fail

How Do You Do It?

Let’s break these down:

1) A goal without a plan is a wish: If you just set a goal (“$X in revenue by December”), you haven’t gone deep enough. You need to specify the – People you need – Processes to build – Dependencies – Timeline Until you do that, you don’t have a plan. You have a wish.

2) It isn’t about the goal, it’s about the habits: A plan isn’t enough to hit your goals, you need to implement. Don’t treat a plan as the exception – make it the rule (or fires will consume your day). Ask: – What routines must I do every week? – What time do I need calendared?

3) Be accountable or fail You’re almost there. But not quite. There’s a reason why a New Year’s resolution to lose weight works if you get a trainer, otherwise not. Accountability. Ask: – Who is going to hold me accountable to the habits?

What’s Next

So now you see how to nail your goals: Goal -> Plan -> Habits -> Accountability Without ALL of these, you’ll whiff your plans in 2023. Or worse, just not bother having a plan and just show up to a dumpster fire in your business every day.

It doesn’t have to be this way. You can absolutely make a change. Just answer these questions:

Have I specified my goals enough?
Do I have the habits to get me there, or do I need to get help installing them?
Who is going to keep me accountable every week?

I’ve been working with entrepreneurs for over 20 years – and the ones that I see make the most progress have found answers to those questions first.

Find out how to be held accountable – and get a weekly list of short, actionable steps to scale your company with simplicity in the Boardroom Bulletin™.

December 20, 2022