Delegate or Die: The 5 Steps to Effective Delegation

By: Jim Roddy, VP of Marketing & VAR/ISV Business Advisor at the RSPA

When the RSPA team talks business challenges with our VAR and ISV members, we hear most frequently about one obstacle. Not cloud POS, not mergers and acquisitions, not vendor relationships, not shrinking margins, not the economy.

The most mentioned hindrance to VAR and ISV growth is delegation.

Flipping through the notes from my last few Strategy Sessions with VAR/ISV executives, I see:

  • a VAR owner stressed out by service calls that pull him away from researching a new, easier-to-maintain POS software
  • a hybrid VAR/ISV CEO asking how he can keep his org’s entrepreneurial spirit alive when he’s not in the room
  • a startup ISV founder running point on both coding and customer service, wondering how he can step away from either without the business stepping backwards

Delegation isn’t just a mindset. It’s a process and a skill. It’s complicated. Multidimensional. And time consuming. No wonder so many SMBs don’t get it right. They either never start down the delegation path or they get distracted and overwhelmed along the way.

To help VARs and ISVs delegate effectively, the RSPA is creating a series of blog posts that will dissect delegation into tangible, digestible actions. This is Part 1 of that series. In addition:


Part 1: The 5 Steps to Effective Delegation

A faulty delegation plan typically involves a frustrated manager dumping a job onto a team member, offering a cursory overview of the task, patting them on the back, and then walking away with fingers crossed things will run smoothly.

The best practice is to slow down and follow The 5 Steps to Effective Delegation: Systemize, Integrate, Delegate, Monitor, Move.

  • Systemize: Design an effective system or procedure for completing the task.
  • Integrate: Integrate the system/procedure into your skill set. Perform the task enough that you are good at it – you’ve worked out the bugs and confirmed it accomplishes the desired effect.
  • Delegate: Teach it to someone else within your organization. Let them watch you do it well.
  • Monitor: Observe them performing the task using your system/procedure. Make sure they are proficient before you stop monitoring closely. Develop reports and/or a check-in system that will allow you to monitor from a distance.
  • Move: Move on to your next initiative with more freedom to continue the growth of the business.

The retail IT channel’s #1 trade show, education conference, and networking event is back! Visit the RetailNOW 2021 website and register today.

Don’t rush through these five steps; each step must be executed thoroughly. The faster you work through the first stages, the less complete those steps will be, and then the longer the last stages will take. And if you rush through all five steps, you’ll find yourself frustrated because you’re not achieving your outcomes which will catapult you back to step one.

Do those scenarios sound familiar? I’m guessing they do because all leaders seeking to grow their business have struggled with delegation at one point (or more) during their career.

The 5 Steps are easy to execute for simple tasks. But complex tasks – especially those that are a combination of procedure and performance – have a much higher failure rate. Let’s map out a detailed example of the 5 Steps framework through a common SMB task: delegating sales. The list below isn’t complete, but it should help jump start your process.


  • Enter contacts and related data into your CRM system
  • Complete sales-related courses through the RSPA Academy EXCELerate eLearning platform
  • Write down your sales philosophies, most effective sales pitches, and testimonials
  • Organize that information into a sales playbook
  • Develop a scorecard that helps determine if a sales call was a success


  • Use the sales playbook to prepare for and execute your sales calls
  • Use the scorecard to analyze your calls
  • Update your playbook and modify your CRM system as necessary
  • Track the effectiveness of those systems; write down success stories and add them to your playbook


  • Task the new sales rep to complete appropriate sales-related courses in the RSPA Academy EXCELerate eLearning platform
  • Prior to each sales call, meet with your new rep to explain your plan and the “why” behind it
  • Make sales calls together with you leading the conversation; request that your new rep take notes during the sales call and complete the scorecard afterwards
  • After each sales call, meet with your new rep to analyze the call, explain why you did what you did, review the scorecard, and answer their questions
  • Repeat this process so the new rep is exposed to a variety of sales calls


  • Follow the same process in Delegate, except the rep is the one explaining their plan, leading the call, and explaining their actions during your post-call meeting; you’re the one taking notes during the call, interjecting only when absolutely necessary, and completing the post-call scorecard
  • Ask the rep to adjust the sales playbook where appropriate
  • Review the notes they have entered in CRM
  • Monitor their performance through CRM dashboards and/or ask the rep to submit appropriate sales reports to you
  • Create a schedule for when you will review reports (weekly, bi-weekly, monthly, quarterly)


  • Focus your time on your highest and best use as your organization’s leader

Your focus throughout the 5 Step process should be permanent delegation of the task to that team member. Provide them the “long version of the story” so they fully understand the situation and can apply principles/best practices in the future. Resist the temptation to short circuit the delegation process by taking over the job. Even if you delay making a sale or miss out on a sale altogether, your business will be better off long-term if the team member learns from the experience.


Two personal notes before we proceed further with the Delegate or Die series:

  • The foundation of this series is the lessons I learned from my employer from 1998-2016, Rick and Terry Peterson of Peterson Brothers Inc., owners of Jameson Publishing and Business Solutions Magazine. Their delegation principles and best practices allowed me to advance from Managing Editor to Operations Manager to company President – and enabled them to focus on expanding their org beyond IT publishing. The Petersons taught several of my co-workers and me about delegation through a 48-page delegation binder (still on my bookshelf), a quarterly offsite meeting, and hours of one-on-one conversations.
  • I first spoke about my delegation struggles as an entrepreneur on the RetailNOW 2016 main stage. Watch a YouTube video of that seven-minute talk by following this link.

Don’t forget to register for RetailNOW 2021, July 25-27 at the Gaylord Opryland in Nashville. It’s Where The Industry Meets!

Jim Roddy is the Vice President of Marketing and a Business Advisor for the Retail Solutions Providers Association (RSPA). He has been active in the POS channel since 1998, including 11 years as the President of Business Solutions Magazine, six years as an RSPA board member, one term as RSPA Chairman of the Board, and several years as a business coach for VARs, ISVs, and MSPs. Jim has been recognized as one of the world’s Top 100 Retail Influencers by RETHINK Retail, a Leading CannaTech Influencer by 420MSP, and is regularly requested to speak at industry conferences on SMB best practices. He is author of two books – The Walk-On Method To Career & Business Success and Hire Like You Just Beat Cancer – and is host of the award-winning RSPA Trusted Advisor podcast. For more information, contact