Prior to his coaching career, Harry served as a product development and design executive at multiple companies and startups such as Rackspace, Virtual Vineyards (now Wine.com), Skype, Dreamworks, Apple, and Hewlett-Packard.
Nowadays, Harry shares his wisdom and rich experience through his roles as executive player coach, consultant, trainer, and speaker.
Prioritization gives you control of the timeline
Harry says that the importance of managing priorities for business is to keep control of the timeline:
"The timeline is what I call the invisible thread that connects the past to the present to the future. And when you lose control of the timeline, what happens is you end up having to react to events as they're happening rather than responding to them in a more intentional and outcome-oriented way.
Prioritization gives you a more perceived control over the timeline, and gives you better options so you can make better plans and decisions."
The DEGAP process
"The process of prioritizing is not a single event. I liken it to animation.
When I worked at Dreamworks, I learned that animation isn't one thing but a process with different phases. And if you're going to skip any of those phases, it's going to come back and bite you later because things won't turn out as well as you want."
And when he looked at the process of prioritization, Harry realized that there are five general steps/phases to it. He calls this process DEGAP which stands for:
- Decide if the benefits of spending the time to prioritize intentionally are going to outweigh the cost of not just acting quickly.
- Engaging in the process by identifying stakeholders and figuring out how you're going to collect the information you need.
- Gathering the information.
- Arranging the information.
- Prioritizing
Sorting items in a sensible way
In real world scenarios, companies deal with various to-dos and needs. A healthy prioritization process helps us sort through all of these in a sensible way:
"Large organizations are never faced with simple choices and trade-offs. They're often faced with conflicting stakeholder views, market issues, imperatives, goals, priorities, and there's never just one of them. So you're often juggling hundreds of different things in different categories at different levels of abstraction.
So the goal of prioritization is to be able to sort through all of that in a sensible way."
The four approaches to prioritization
"If you look at prioritization through any steps, it follows the same steps as DEGAP. But when we talk about the taxonomy that holds prioritization together, there are four different approaches."
- Sorting techniques
- Visual frameworks
- Marketplace simulations
- Hybrid methods
Sorting techniques
Sorting techniques are approaches where you sort items using a specific set of criteria. These techniques are more algorithmic and more mathematical.
Examples of sorting techniques are stack ranking, paired comparison, and RICE/ICE.
Visual frameworks
Compared to sorting techniques, Harry says visual frameworks have dimensions like importance versus urgency.
Examples of visual frameworks are Luke Holmann's Prune the Product Tree, the Eisenhower Method, and the Max Priorities Pyramid.
Marketplace simulations
Marketplace simulations help you simulate how something might play out.
One example of a market simulation approach is to use Monopoly money to buy a feature.
Hybrid methods
Hybrid methods combine the above mentioned approaches. One example of a hybrid method is the analytic hierarchy process.
"You can also sequence in or possibly develop tournaments where you're using different sorting techniques, visual frameworks, and marketplace simulations in some kind of order to produce a more sophisticated result."
How to select evaluative methods
How do you deal with projects with different natures using similar criteria?
Rather than a straight ordinal list, Harry advises to use evaluative methods that's something similar to the Fibonacci sequence. This will give you large distinctions when comparing items:
"If you're using an ordinal evaluative approach, you can't really differentiate between small, medium, large, and extra large because it's very subjective.
But when you use something like the Fibonacci sequence, you end up with something from maybe 1 to 144, where the distinctions become increasingly large. It makes it a lot easier for you to say, 'We're going to compare this thing that's obviously much larger to this one that's obviously much smaller.'"
Harry adds that selecting the right method becomes critical to estimation and essentially helps you make the smarter decision:
"Identifying the distinctions is critical when it comes to estimation. It's critical in assigning values to the attributes for each item.
It's also part of why slowing down the process and being more intentional is so crucial to creating better plans and smarter decisions."
Are we really bad at prioritizing?
"I get asked all the time, 'Why are we so bad at it?'
And my answer is, we're not. We're actually brilliant at prioritizing but at simple, static environments. We're terrible at it in large, complicated, organic, and adaptive environments."
So when we compare working with only a co-founder versus a large organization, it's often easier to adjust in the first situation when prioritization is wrong.
"In a situation where it's just you and a co-founder, it might be simple and static enough that it isn't too hard to just pick something, run with it, and adjust if the prioritization is not right.
But in a large environment, there's a very good chance that you're not going to know that it's wrong until it's too late. There's even a better chance that once you've figured that out, the results of being wrong and it being too late could be catastrophic."
How wrong prioritization affects a large organization
Harry uses a hiring example to illustrate:
"I'm currently working with a CEO who hires quickly because he's trying to solve a problem. He doesn't get really clear about the criteria, and he doesn't run a healthy prioritization process.
When things go wrong, he takes a terribly long time to let the person go because he doesn't have a rich process model for holding the person accountable, for evaluating them over time, and from learning from his own mistakes."
Without having a healthy prioritization in place, it makes it difficult to fix the front end of the process:
"The time between the decision and the outcome could be so large that it's very hard to fix the front end of the process because you don't realize that's where the problem is.
You think the problem is with the person, but the problem is with your process."
Final advice
Don't read your email, Slack messages, phone, or the news first thing in the morning.
"If you do any of those, that guarantees that you're not going to prioritize as effectively as you can."
Do spend the first 30 minutes of your morning organizing yourself and prioritizing the tasks for the day.
"The morning boot routine is a lot like mise-en-place, which is a process a chef uses to prepare everything they need for cooking."
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