Stakeholders Unite! 5 Must-Haves for a Winning Software Discovery Workshop

Oksana Cyrwus
Software Solutions Architect
December 06, 2019

Delivering a great software product ahead of schedule and under budget isn’t exactly rocket science. But it does begin with people-science.

Our job is to deliver strong results. Our clients must be satisfied.

Any seasoned software professional should understand that you cannot solely rely upon an RFP as your initial scope guideline. Very often, the client’s portrayal of hi-level organizational goals is not fully articulated within the context of the formal document.

This is not error, but incomplete process.

We also need to account for unforeseen impediments, newly available research data and the likelihood of sudden change.

For more than a decade, I’ve helped build software products contributing as engineer, project manager and solutions architect. From being just one “gear in the machine” to having my “head on the chopping block”, I’ve leveraged my success - and failures, along with a multi-perspective viewpoint into a process standard that will better enable teams to deliver world class products with minimal refactoring, minimal change orders.

Oh yeah, there’s lot’s of winning involved, so be prepared for some serious stakeholder love. Winning tends to bring people together, after all.

So that’s a tall order, but doable. How so you say?

Well, in my world, a great software product begins with a great Discovery Workshop.

Stakeholder alignment is absolutely essential to product success. Given how the selling points as to the feasibility of gathering all stakeholders into a face-to-face collaborative environment are near infinite, you have nothing to lose - everything to gain.

So here we go - you won’t find any technical advice in this post, but you will find 5 must-haves for a winning software discovery workshop.

Attendance! Attendance! Attendance!

Once the contract is awarded - immediately begin planning the event!

The main goal is to properly identify the appropriate stakeholder attendees in order to extract the maximum value of information within the allotted time.

A physical on-site location is required. No exceptions. Make it easier on the client by hosting, or co-hosting the event in their hometown.

Time duration of the workshop will remain relative to the scale and complexity of the project. However, by planning the event over the span of several business days, you provide a level of flexibility that ensures the appropriate level of attendance for all.

As a standard practice, the vendors team will hammer out the list of required attendees. Make it as inclusive as possible, but within reason. Keep in mind, the more attendees, the more time you’ll burn up.

Inevitably, there will be scheduling conflicts to where key stakeholder participation will be limited. Be flexible. Be firm.

Getting pushback? Reiterate the necessity to install a unified framework of ideas that will streamline events throughout the entire project span resulting in higher quality with lower operating costs - and that all designated stakeholders must attend.

They’ll shine like the sun when it’s all said and done!

The Social Primer

Attempt to construct an atmosphere of trust.

Before the onslaught of high level departmental goals and associated risks and impediments, you will want to set the proper tone for healthy long term collaboration.

According to a study performed by, the average software project, from conception to delivery, requires 4-9 months time. Often more.

Stop and think for a moment. If you’re committed to collaborating with a new, or even familiar, client team for a 9 month span, you will likely find collective benefit to laying the groundwork for trusting relations.

An open group format helps neutralize the introverted, extroverted component. So don’t just announce your name and title. Take it a step further. Share some ideas related to your personal or family life. Maybe a quick tale of non-professional interests that inspire you. Share the name of your dog/cat/parrot or any other details which makes you who you are.

The social primer helps reveal team members’ individual character as well as communication style. Simple, open conversation at the beginning of the discovery workshop will help lay the groundwork for building trust, respect and empathy toward one another.

Pay attention. Share humor. But don’t just listen attentively. Interact. Take notes to better solidify your understanding about the people you’ll be working with - you’ll be glad you did.

Push for Open Collaboration

Now’s the time to get to work.

Interdepartmental collaboration is the centric action.

Stakeholders will often bring their ideas to the table promoting their distinct objective, often without a balanced view toward the collective cause. This holds especially true for departmental representatives with their own KPIs to track that may be irrelevant, or unknown, to other team members.

The ultimate goal of the discovery workshop is to define the highest product value in accordance to available resources. Getting the entire team to commit to a formalized definition of value is the big challenge.

Expose the bias. Build a shared belief.

Often the discussion is quickly skewed by one or two dominant persons within the group. Here you may need to inject a socratic response so as to enable others to better intervene in an effort to expose conflicts and establish priority features of the software product.

Not only are you assessing priorities according to value, you’re also managing personalities, responsibilities and ambitions.

Here’s where the emotional intelligence factor begins to shine.

Define the Meaning of Success

Co-create a shared understanding.

Collaboration isn’t about advocating for a particular point of view. It’s more so related to exploring all the unique, individual perspectives within the room, then doing the work to co-create a shared understanding.

Optimum progress is achieved once the goals and methods of goal measurement are clearly defined.

Studies have shown, when humans have properly set goals to guide them, they are happier and in turn achieve more than they would without having them. Having goals provides focus and a measuring stick for progress.

Software projects are much like humans. They must have clearly defined goals and outcomes to be effective.

The most common reason for a software project’s failure isn’t necessarily blown budgets or timelines. It is the failure to align the project with concise business goals.

A discovery workshop is the best time to dive deep into the business layer and get clarity and alignment on what success looks like for the project. Not everybody has the same definition of success. Some prioritize target cost/time, while others consider user adoption capability, conversion rate or innovation capability to be priority.

Be clear about the benefits you’ll bring your customers. Prioritize only those features that will bring these benefits. Set milestones and commit to milestone goals. Define KPIs. Optionally, define a Minimum Viable Product (MVP).

Be analytical, be creative! But most importantly, commit and be accountable.

Adopt the Continuous Discovery Mindset

What if I told you that Discovery is never really complete?

Some of the Agile principles are continuous iteration and adaptation to change. I bet if you look back at your experiences running agile software projects, you’ll recall that requirements can change almost every week and not just by the client’s initiative. And according to Agile - this is the norm.

So what is Continuous Discovery?

Continuous Discovery is a mindset and it is a process. It involves frequent touch points between the client and the team who is building the product. We want to engage the client every week instead of saving a bunch of questions for a bi-monthly/monthly demo or review.

If we want to move fast and remain client-centered, we need to engage with our clients every week. However, as many within the software industry can attest, this is not how many teams operate.

Too often we adopt a validation mindset. We believe that we’ve solved our client’s problem, then we validate it with them - and move on.

However, if you continue to engage with your clients more frequently, you’ll develop a co-creation mindset where the client will better collaborate with your team, improving the effectiveness of all.

Don’t get confused, you’re not looking to your client to tell you what or how to build. But you are collaborating in order to integrate their perspective into your team’s perspective.

It is important to instill the concept of Continuous Discovery during the Discovery Workshop. This helps stakeholders open their minds to new ideas, new methods of collaboration, commit to a set schedule and ultimately helps you deliver a product you can be proud of.

Have a project in mind, but not sure where to start?
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Ever Forward

Discovery workshops are just one component within our best practice toolkit that enables us to deliver highly effective software while building meaningful client relationships.

These 5 Software Discovery Workshop tips will help you kick-off the project properly and get teams focused on delivering real value. Naturally, there’s much more that goes into a successful Discovery Workshop, all of which is dependent upon your specific working arrangement.