3 Lessons Learned in Delegating, Scaling Up and Cracking the Whip as an Entrepreneur

As a serial entrepreneur who has built (and lost) multiple businesses over the past 20 years, including growing my current company - Ward Law - to over 200 employees, I've learned some valuable (and sometimes painful) lessons about delegating, scaling up operations, and yes, even "cracking the whip" at times. I want to share a few key insights that have been instrumental in my own entrepreneurial journey.

Lesson 1: Hiring People Better Than Yourself

When I first started out as a “solopreneur” working from my garage, delegation wasn't even on my radar. I was the quintessential "dominant personality" entrepreneur - I knew exactly what I wanted and I took action to make it happen myself. Bringing in my first partner was a big step, but even then, true delegation was a struggle.

It wasn't until about eight years ago that I had the critical realization that changed everything: I needed to hire people who were better than me at the specific functions I was hiring them for..

And if they were better than me, I had to get out of their way and let them do their jobs. This was a tough pill to swallow for someone used to being the best negotiator, the best manager, the best litigator, the best bookkeeper, the best everything in my business.

The Magic of Letting Go

But once I started letting go and allowing my team to shine in their areas of genius, magical things started happening:

• We started making more money
• Things ran smoother
•  People were happier and more productive

I realized that as a leader, my job was to set the strategic vision, put the right people in the right seats, and then let them drive the bus. My job was to ask questions, not bark orders.

Lesson 2: Balancing Inspiration and Accountability

This brings me to my next hard-earned lesson: you've got to be willing to "crack the whip" as a leader, but in the right way. 

I consider myself more of the nice guy, focused on inspiring people to be their best selves. But I learned that I also needed some key people under me who were willing and able to hold people accountable, push for results and enforce performance standards when needed. You need that balance of inspiration and perspiration to scale up successfully.

Accountability has become one of our core values.  We look for accountable people when hiring.  But our focus around accountability is to inspire the people to hold themselves to their level of accountability, not to impose our will on them.  This is tricky because when the job isn’t getting done, it is easier to crack the whip in the short run.  Learn to look for the balance between drive and inspiration to get the job done.

Implementing Systems for Scale

Which leads me to the critical importance of processes, systems and checklists as you grow to ensure the job is actually getting done. 

In the early days up to about 15-20 employees, simple checklists can work wonders just to make sure everyone is following the key steps. But as you add more people and layers, you need to start documenting and delegating multi-step processes within and between departments.

This can feel tedious or micro-managey, but the truth is, most employees need and want clear direction. They need to know exactly what a good job looks like, whether that's how to answer the phones or how to clean the windows. Freedom and autonomy are important, but you have to first provide the basic framework for success.

So how do you do that?

We've learned to build our processes organically. We started with one simple checklist, then added one more the next day. Over time, those have evolved into the sophisticated systems that now run much of the company. But it all started with those basic checklists to ensure consistency and accountability.

Lesson 3: Every Touchpoint Matters

Beyond that, I'm a big believer that every touchpoint in your business can and should reinforce your core values and help "close the deal." 

For example, what is your on-hold music or message communicating to callers? What scripts are your receptionists using when they pick up the phone? Every interaction should convey your unique value proposition.

In the end, embracing these sometimes uncomfortable changes as a leader - delegating to those more capable than yourself, finding the right balance between vision-setting and whip-cracking, implementing scalable systems, and maximizing every small touchpoint - is what allows you to grow from a solo operator to running a thriving company.

It's never an easy or comfortable process. But if you can fight your instincts to control everything, put your faith in the right people, and create an environment of both inspiration and accountability, you'll be amazed at what you and your team can achieve together. 

The entrepreneur's journey is always a winding path, but with the right mindset and practices, you can navigate the obstacles and experience incredible rewards.

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