How to Hire Your First Head of Business Operations and Take Your Success Up a Notch


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Hiring your first head of business operations can be a daunting task. Your head of business operations is an important partner in the leadership of your organization, someone you trust to run the day-to-day operations. If you don’t hire the right fit, you’re going to be miserable.  

Where do you start? How will you know you can trust the person? What should you be looking for? These are the top questions I get from entrepreneurs on this topic. 

The needs for this role can vary greatly, but the approach can be rather straightforward. I should know: I’ve been a director of business operations, general manager, chief of staff and a COO! 

I’ve also consulted numerous companies hiring their first operational leader. This should be one of the most exciting times in your company’s lifecycle, so let me help get you started on that path. 

Related: The Key to Hiring the Best Employees

Here are the top three things you must do when hiring your first head of business operations:

  1. Leave strategy or strategic initiatives out of the job description.

  2. Create a hiring toolkit.

  3. Use a 30-60-90 day onboarding plan.

Role design 

Do a quick search on job postings for head of operations — I bet you’ll find several postings that advertise “head of strategy and operations.” But this approach leads to turnover.

People that have strategic skills love to build, not operate. So, when the initial strategic initiatives you have planned are completed, and their day shifts to just operating, they will grow unhappy and leave.

If your budget is under $120,000 for this role, it is unlikely that person will have the strategic skills to be head of strategy. You will start to notice he or she isn’t gaining traction on those strategic items, and your relationship will start to sour. 

You’re the entrepreneur; new hires should be integrating your vision into the business — not the other way around! Keeping that role design focused on operations allows you to concentrate on what truly matters in your business. Find someone with industry expertise and a track record for results running day-to-day operations.

Related: 6 Tips for Hiring at Your Small Business

Hiring toolkit

This is not a role where you should be looking for shortcuts. Be sure to put in the time and prepare a comprehensive hiring toolkit. You should have the following items prepared, at a minimum:

  • Job description. Remember, leave out strategy! Have it focus on running the specific day-to-day operations of your business. 
  • Candidate profile or avatar of your perfect candidate. Find a real person on social media and create your profile based on his or her features and strengths. 
  • A work assignment. Ensure the person’s skills and expertise match the interview experience by asking the person to complete 3-5 case studies. 
  • Prepared interview questions that dig in deep. Remember, you are interviewing the candidate, not the other way around! He or she should be doing most of the talking.

Onboarding plan

Lastly, the number one mistake I see entrepreneurs make during this hiring process is leaving their new operational leader to his or her own devices. Start your relationship out strong by following an onboarding plan. 

This plan should cover the first 90 days and key milestones for success. Here’s a simple framework to get you started.

Day 0: Discovery

New hires should learn about the company, competitors, the products and services and their team. 

Include a list of their top priorities:

  • Review any relevant documentation — company handbook, strategic planning, go-to-market materials, etc. 
  • Research the team by reviewing resumes or LinkedIn profiles.
  • Review competitors.
  • Test the product(s), if possible.
  • Access internal-communications platforms and other relevant tech systems.
  • Workstation setup — laptop, speaker, webcam, mic, ergonomic desk and chair.
  • List the milestones for completing those priorities.  

Days 1-30: Assess, plan and maintain

 Gain a full understanding of business operations and systems in their current state. Identify critical business risks and opportunities for streamlining operations while maintaining any current systems or initiatives. 

Include a list of their top priorities:

  • Meet with the entire team and leadership with the above focus in mind. Set ongoing meeting cadence.
  • Conduct one-on-ones with all direct reports.
  • Get up to speed on any planned initiatives. 
  • Learn any existing systems.
  • Experience the product and collect learnings.
  • Address any critical issues with a short term plan and implement where appropriate.
  • Review relevant financial statements, models, processes and procedures.
  • Conduct a complete assessment of operational infrastructure. 
  • Document all risks, gaps, ideas and opportunities.
  • List the milestones for completing those priorities, like a go-forward plan. 

Days 31-60: Execute

 Execute upon the recommendations for addressing business risks and streamlining operations.

Include a list of their top priorities:

  • Iterate on the go-forward plan with CEO and leadership.
  • Make execution decisions on the proposed projects and initiatives in the go-forward plan — timing, resources, etc.
  • Review and kick off development plans with all direct reports. 
  • Maintain execution on any existing initiatives underway, perform post mortems on any completed initiatives. 
  • List the milestones for completing those priorities.  

Days 61-90: Elevate and grow 

Start working out of appropriate management areas by elevating members of the team while developing a team-growth plan for the next quarter. 

Include a list of their top priorities:

  • Identify high achievers on the team and start coaching them for elevated responsibilities.
  • Test, collect learnings and make improvements.
  • Identify growth opportunities and areas of innovation. 
  • List the milestones for completing those priorities.

I hope this approach already has you feeling better about this big decision, where you can start and how you can ensure trust in this role. If you focus on operational responsibilities in the role design, prepare a hiring toolkit and write a 90-day onboarding plan, you will be set up for success. 

Related: If You’re Not Hiring Ahead, You’ve Already Fallen Behind

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