From The Cannabis Diaries #2: Let The Right Ones In

Updated: Jul 11, 2019



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We often talk about Technology as a crucial component to businesses and organizations. Software, hardware, frameworks like Agile, or trends like digital transformation are simply tools. Technology tools, applied to your work, either make life easier or they make life harder.


The people that architect, design, develop and operate these tools are critical to an easier workday and better business results. Bad IT hires can have a catastrophic impact on your organization. Once you hire a bad IT resource, getting rid of them can be difficult.

One of our cannabis clients was investing in their technology team. Prior attempts to identify a Chief Information Officer (CIO) that could deliver had failed. My role was to improve IT services, get the team on track, and find a full time CIO that could drive the transformation roadmap.


Unfortunately, the two prior CIO candidates were still around. Three factors made them almost impossible to remove:


  • They had access rights and administrative control over critical business systems.

  • Almost nothing was written down, making it impossible to recover or transfer knowledge.

  • Technical jargon and complexity provided them with time to plant deep roots.


Rather than ripping these individuals out, most organizations choose to leave them in place and work around them. This is a tremendous waste of time and energy, particularly given the price of IT resources in the current labor market.


For example, entry level resources in San Francisco and Oakland start at $100K+ USD. A tech team of 3 would conservatively add $400K in payroll, assuming one senior resource. Can you afford to stick with a bad hire at that burn rate?


One of our client’s desktop support staff was deeply dissatisfied with their role. They considered their business colleagues inept and stupid. When the manufacturing site lost their network, this individual refused to drive down the street to help restore service.


The Chief Operating Officer (COO) of the company had to climb a 20 foot ladder to pull information off of the router and spend hours on the phone with Verizon. The COO was livid, and I heard about it a few days later. We had a toxic IT hire that was hurting our business.


Here are some key interview questions to help you avoid pretenders, especially as experienced IT people are clamoring to enter the cannabis industry:


1. What results have you delivered?


Answer 1:

“I helped our business implement an online e-commerce tool and a new point of sale system for dispensaries. We set up a rewards program to improve brand loyalty. We spent about 6 months and $250K, but we saw a 3X increase in sales and customer satisfaction. Our sales people are happy, our customers are happy, and we did a good job. We had some problems, but we managed to sort through initial concerns about online orders. Once salespeople saw that they’d make more money by getting a cut of in person and online sales, they got on board. Once customers saw that their privacy and security were a top priority, we saw orders rise rapidly.”


Answer 2:

“Not my fault. If they would have listened to me and bought FancyTool, it would have gone well. FancyTool is the only way to secure and transform a business. Digital transformation is cool, although I cannot give you a concise definition of it. We had no problems, other than the business changing their mind on requirements after we went live. We spent another two months writing enhancements and releasing hot fix updates to the software. If they’d just use it properly, everything would be fine.”

Who would you hire? “Me, me, me” answers are a red flag. Avoid hiring technology staff that do not clearly understand that technology serves the business, not the other way around.


2. How does this person align with the job description?


If you want to increase sales, how would this hire help you achieve those goals? If you want to be known as a safe, secure provider, how can this person help you build that reputation? Business and technology people often speak separate languages. Be clear in your goals in common sense, business terms. Write down the top two or three. Gauge their ability to give a thoughtful, considerate reply.


Good Example:

We are hiring a technology team member to support the business and drive technology. In the first 3 months, we would like to accomplish the following:

  • Fix recurring issues with the network, particularly dead spots in cultivation sites and slow internet at the warehouse.

  • Diagnose and understand problems with QuickBooks.

  • Prepare a sales dashboard to help manage salespeople and online orders.

  • Link customer demand with cultivation R&D and product development.

This example provides a timeframe to set and manage expectations. If the interviewee has reservations about accomplishing these items in 3 months or less, they should begin to ask questions to capture your assumptions.


  • How fast is the internet going into the warehouse?

  • How long have you been having the QuickBooks issue? What is the problem?

  • What do you use to manage the sales team today?

  • What do you use today to plan yield and production?

This example is a combination of short term, relatively quick fix issues that are urgent (no internet = negative impact on operations) and more strategic issues (sales dashboards require training, incentivization, and alignment with managers to measure the right behaviors).


View the job description as a loose (or hard and fast) contract used to assess results. As a consultant, I am graded on my deliverables. Employees are not consultants, but clear expectations, defined problems, and measurable outcomes drive higher performance.


3. What would your priorities be at the beginning and how would we set those together?


If they have been paying attention, the interviewee should be able to articulate their approach to collaborate with their colleagues to achieve your goals. This should be a candidate’s time to shine and demonstrate the art of the possible. As technical subject matter experts, they should be able to align specific software, hardware, and frameworks to fit your goals.


Listen for the tools and solutions that they mention. Would you hire a Python developer if your systems were written in C#? Would you hire someone to support Google Suite products if they have only supported Microsoft Office organizations? Would they adapt to your working style or would they require a ticket before they support a colleague?


When I was interviewing CIO candidates for the full time role, I asked about the typical team size that the candida tes were used to managing. CIO candidates who were used to running large, globally distributed organizations were not automatically disqualified, but I needed to hear more about their ability to operate with a growing, small team. If a candidate was not used to rolling up their sleeves to run a project or repair a network, they were not a good fit.


A number of candidates entered the discussion with a pre-set, ambitious agenda. With a list of 30 initiatives, the number of big ticket projects on their agenda would swamp the business. Setting 2 – 3 priorities every few weeks, rather than 10 – 12 priorities per person, will ensure that the technology hire can focus. Once they are done with those priorities to your satisfaction, work out the process for how new work is added to their plates.


In summary, you need to write down and understand your requirements, goals, and the responsibilities before letting an IT professional into your organization. Their levels of access to information and core systems make them far riskier than almost any other type of hire, outside of sales and your social media account manager.


Ask for their results, see if their skills fit your needs, and set a clear list of priorities for the first 3 months. Applying these methods will help your cannabis organization find a better fit and avoid being the harbor for people drummed out of other industries or companies.

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