Good technology decisions: A framework for CFOs and other non-technical leaders

Nate Parsons2/28/2025

Increasingly complex technology decisions can make or break your organization, but you don’t have to be a technologist to get these right.

These days most organizations are asking their non technical leaders to make or approve major technology choices, and that person in the hot seat might even be you! Some data:, Robert Half reports that “70% of technology decisions now involve CFOs, Furthermore, 60% of CFOs say they are the ones responsible for underlying technology decisions to achieve business results, signalling a shift in how decisions are made.” The reality is that even if you are a departmental VP, CEO, President, or Executive Director, chances are good that you’re going to be asked to make an enterprise wide technology decision that you aren’t 100% comfortable making.

Any normal person would feel some anxiety and uncertainty when asked to weigh in on something complex, technical, and unfamiliar. A normal person might even decide that not making a choice would be less risky than making a wrong choice. Data from Microsoft tells us that a lot of leaders do just that, from a recent report they published: “79% of leaders agree their company needs to adopt AI to stay competitive, but 59% aren’t sure how to quantify the value of investments and 60% acknowledge they lack a plan and vision to implement AI.” This is just the anxious technology choice of the moment however, and wouldn’t it be nice if you have a framework that ensures these decisions aren’t so hard to make, and to make well consistently?

What’s stopping you from making good technology choices?

The biggest reason that these decisions aren’t made well is that most leaders don’t have a decision making framework to guide how a good decision can be made, and they instead feel a huge amount of personal pressure to MAKE the best decision themselves. This approach rarely results in the getting the right experts, priorities, and business limitations in the room together at the right time, and it usually distracts leaders from the more important decision USING process they need to steward and using their position to support.

Without a decision making framework, you as a leader will be tempted and motivated to try and become an “arm chair” technology expert so that you can feel more confident making a stressful and high impact decision.

But guess what… Successful technology choices need leaders whose mantra is “My job is to ensure the best decisions get made, not “I need to make the best decision”

By focusing yourself as the steward of the technical decision making process, you free yourself from feeling like an imposter that you don’t understand the technology, and at the same time you empower yourself to really add value, perspective, and structure to the technology choices for the organization. Your leadership role is essential because as intricate and complicated as some technology choices can be, the business priorities, and the goals the business have also need to be translated and clearly presented as inputs into the decision making process in order for good outcomes to occur.

That is both good and bad news. Let’s start with the good news: You personally have the power and agency to ensure your business makes great technology choices while reducing failure and risk rates! The dirty little secret of successful technology use isn’t that technical geniuses are involved, but that technology choices are made in harmony with the business’s goals, limitations, and needs. Now the bad news…making good technology choices likely requires changing the way you and your organization make technology decisions, and how you support these decisions once they are made. This is because there is no “one size fits all” approach for technology decisions. There are in fact three sizes that you need. =)

The three bears of technology decisions

Small Decisions - Internal to one department, or choices impacting how your implementation staff operate
Medium Decisions - Decisions that will impact multiple departments or teams. These decisions frequently can’t proceed without your active executive sponsorship. These fall into two major subcategories:

-- Decisions of unclear business value but obvious risk, where you as an executive need to be the adult in the room ensuring all the pessimistic questions and “have you considered this?” questions are asked.

-- Decisions of obvious business value, and currently small/acceptable risk that need you to help advocate for them to be made, while defending them against feature creep, bundling with other less desirable work or decisions, and executives who feel like they need to insert themselves into the process

The Big Decisions - Large choices that will impact your entire org, often are driven by strategic plans, board of director inputs, or CEO goals, and occasionally due to market conditions. You’ll be able to identify these by the sheer number of decisions that need to be made.

This handy chart helps illustrate how these projects play out between project complexity, potential business impact, and offers an example of each size of project.

You can scale each axis based on your role within your organization

I’m sure you’ve noticed that each of the three decision areas has a specific management approach labeled with it.

Governance

Description: - Decisions made by empowering your staff to make the right decisions for their local needs, where they have the most day to day expertise and are responsible for efficiency and quality. You can tell when you’ve reached the useful boundaries of governance when decisions mean multiple teams existing governance & SOPs will be impacted.

Leaders - Your job as a leader here is to provide your staff with the right guidance on how to document these decisions, message them properly, and ensure that they have practical change management processes internally. Much of this is about letting your local experts create value with as little friction as possible by setting up standards for these decisions to be evaluated, communicated, and documented routinely.

Active Engagement

Description - Decisions that will impact multiple departments or teams, where coordination of not just the technology, but the leadership personalities involved, the personal and professional goals of leaders, and the reporting & messaging of these decisions plays as big an impact as the choices themselves do. The kinds of decisions that require inter-departmental cooperation. Most of these decisions will have either an intricate refinement to an existing business process or require changing cooperative rules between departments for shared infrastructure.

Leaders - When business value is uncertain, and risk rises above an acceptable threshold, leaders work to interrogate the decision making process and ensure proper diligence happens, especially regarding inter-departmental impact and change management costs on projects, often being the useful “negative nancy” in the room. Did your experts and practitioners really consider everything? Did they confer with colleagues in impacted downstream departments? Conversely, when the business value is certain, and the organizational risk is acceptable, executives actively engage to ensure the projects or decisions remain so by beating off feature creep, other executives inserting themselves into the process, and/or “bundling” of work. Many a good decision has become a bad one due to bloat and “can we do this other little thing at the same time?” additions.

Measured Outcomes

Description - Decisions so large, so vast, or so far reaching that the implementation of the work, and the outcomes produced, must be measured over time and assessed based on those measurements. These projects typically require multiple experts in different domains to make decisions, and thus are ones that won’t be successful if they are “owned” by one executive.

Leaders - When executives identify projects that are very complicated, they ensure that the projects are managed and evaluated against metrics & measurable outcomes, moving “subjective” success and support out of the picture, and working to build executive buy-in and acceptance of those metrics as the deciding factors. These projects are too complex for most executive leaders to evaluate the merits of the approach or execution and that means you need to ensure that everyone is evaluating against things they can understand and evaluate, i.e. metrics. Leaders here need to champion and advocate real objective measures of performance, and build buy-in from the senior executive team to abide by these metrics as the definition of success & failure.

The decision making framework for non technical leaders

Your involvement should scale with the decision's complexity and potential impact. For low-impact decisions, light-touch governance is sufficient. As complexity and risk increase, shift toward active engagement while maintaining focus on goals rather than implementation details. As projects scale to the largest size, you move from actively engaging with just your team, to actively engaging with the executive leadership team as a whole. Remember that this framework is dynamic. Regular reassessment of decisions and their categorization ensures your governance approach remains appropriate as circumstances change.

You should adjust your leadership approach based on the clarity of impact and risk

Governance - Low Risk, Unclear Value

Your best approach for many low risk, unclear value, often internal to a department sorts of decisions is to empower your staff with clear boundaries while giving them the autonomy to make as many decisions as they can for themselves. By setting basic governance guidelines that define the outer limits of acceptable choices, you let your technical experts innovate within those parameters. This approach builds trust, speeds up delivery, and allows for frequent internal experimentation without putting the organization at risk.

For this to be successful you need to allow for some team flexibility in spending, staff allocation, and “internal change management” often paid out in the form of technical debt remediated. I.E. if the team wants to subscribe to some $20/month service they think will really speed things up, and they’ve thought through data privacy, security, etc angles, they should be able to do that without you having to hear about it at the point of decision, but be made aware of it through a routine review process per/quarter. Equally, if they feel like it's important to get in a room and remake a spreadsheet template they use frequently, let them at it.

Goal: Allow experts to make many good internal decisions in an organized and thoughtful way, while ensuring major decisions are properly escalated and identified for further review.

Leader actions

Define clear governance boundaries, cost, and acceptable risk parameters
Create standardized evaluation criteria for teams to self-assess their choices
Establish regular review cycles to ensure decisions stay within guidelines
Empower staff to maintain operational metrics, or surpass them.
Identify areas where you might be over-governing low-impact decisions and remove bureaucratic friction.

Staff actions

Perform self assessment of proposed change - this assessment should act as documentation as well, and be published to the intranet
Maintain onboarding & training materials in sync with current SOP/Governance
Identify choices that rise above the governance boundaries & require more active leadership involvement

Types of questions you should ask:

How will costs scale year over year?
Are there alternative solutions in case the current low cost solution folds?
Did you document which solutions are integrated with each other in case a major business system has to be replaced in the future?
Did you update our documentation on which services we use, and the licensing details in our intranet?

Active Engagement - High Risk & Unclear Value

Encourage your teams to be forthright about challenges and progress. Create an environment where honest metric reporting is valued over comfortable operational updates. This transparency helps identify issues early and enables better decision-making. It’s especially important when you are confronted with a decision with murky value, but obvious risk.

Goal: Ensure decisions that don’t need to be made, aren’t and that decisions that are half baked get fully baked before being made.

Leader actions

Investigate the decision with your staff experts and stakeholders to really understand the value proposition. Not infrequently choices presented with obvious risk and dubious or unclear business value are choices that need additional refinement & definition before they should be made.
What you want your staff and stakeholders to help you understand (and understand for themselves) are what are the perhaps less satisfying, less elegant, and yet totally acceptable choices that are available that can limit risk, while clearly defining the business value of making the choice.
While it’s not all about being a pessimist, many a “we have to replace this system” announcement from staff has turned out to be something more like “we have to do this un-satisfying work around, but it works fine and was really cheap to do” after some investigation.
Your primary job here is to make sure that the unclear becomes clear, and then to have everyone honestly appraise the value of that choice with everything on the table.

Staff actions

Provide clear descriptions of the problem that must be overcome, and the various approaches they’ve identified for solving that problem.
Conduct analysis on the feasibility, effort, cost, and disruption of each approach
Research how other organizations have addressed this challenge.
Think of ways to mitigate any current negative impacts and allow more time for the decision to be made.
Develop evaluation criteria for each approach that allows each one to be semi-objectively rated or assessed.

Types of questions you should ask:

Walk me through the business value proposition:
Walk me through the research you’ve conducted into how our peer & competitor organizations have solved similar challenges
What are our different options for how we could implement this, and what are the pros and cons for each of them?
What’s the cheapest way to do this, and why wouldn't we do that?
What’s the most cutting edge way to solve this problem?
What’s the industry standard way of solving this problem?
Tell me how you’d solve this problem at X budget, ½ of X’s budget, and 3 times X budget.

Active Engagement - Low Risk & Clear Value

When you are lucky enough to be presented with a decision with low risk and clear useful value, it is easy enough to make the right decision. However these decisions often need ongoing executive support and defense during implementation to ensure they don’t get derailed. At bigger businesses in particular it can be the case that everyone agrees to an improvement, and then it’s still not implemented and delivering improved business results after a year.

Goal: Ensure real change happens in your organization by ensuring the easy value adding decisions are implemented without delay and start returning value as quickly as possible.

Leader actions

Ensure the decision remains as simple and clearly defined as possible by defending its implementation against bundling with other decisions, edits by other executives, and attempts to delay execution.
Prioritize staff time to get the results of the decision implemented and in production as quickly as possible.
Adjust budgeting & staff resourcing as needed to support execution of the work.

Staff actions

Provide a clear implementation plan with dates, staff resourcing, and milestones
Avoid letting the “perfect” be the enemy of the good, focusing on getting improvements into place now, vs even better ones at some obscure future date.
Alert leadership to attempts by other departments or executives to add to or adjust implementation details
Alert leadership to foot-dragging or fiefdom defending practices by other departments that hinder execution

Types of questions you should ask:

What day to day operations or ongoing responsibilities will be impacted while implementing this work.
What additional support/capacity will be needed, such as vendors, freelancers, or staff time from other departments?
What other departments will you have to liaison with, and what working relationships do you have in place (if any) with those departments? Especially in areas of training, or existing standard operating procedures those other departments have impacted by this work.
What other projects/tasks do your vendors have that they might balance against any implementation work you need?
Do you foresee any friction points with other departments or executives?

Measured Outcomes - High Risk, Clear Value

When dealing with high-stakes decisions, resist the urge to micromanage the technical details. Sure there will be a lot of important point decisions, but you aren’t the best person to be making those. Instead, you should focus on ensuring that the executive team clearly communicates what success looks like and establishes metrics that matter to the business. Your goal is to provide an evaluation framework that can be used by many technical experts up and down the line of execution of a major decision. You want all your staff in alignment with business objectives, using their expertise in the service of a well understood goal. This will yield far better results than your arm-chair quarterbacking of a million technical details that you’ll never fully understand.

Goal: Address and resolve the most common reasons major decisions fail, and ensure the non-glamerous grunt work of major change and risk management is conducted, all while ensuring executive sponsorship remains firmly attached to major decisions.

Leader actions

Set clear, measurable objectives - Often this will require someone like you taking the first stab at drafting these and then stewarding them through the executive leadership team to gain consensus approval of a revised draft. This is typically where these big projects either fail or succeed, because they require multi-departmental support.
Define risk appetite for implementation complexity - are executives ready for the change management, adoption, migration, business disruption, branding changes, etc, involved in this decision? How radical can your changes be?
What is your escalation strategy for pushing issues up through the chain of command or implementation?
Maintain regular check-ins on progress toward goals - you want to position the executive team as working to solve the problems of these major projects, so resist the temptation to report on the project as if you own it.
Create transparent reporting mechanisms - you can’t solve the problems you never hear about, and far too many companies shoot the messengers. Work hard to make sure everyone feels like the whole company is working to make this project succeed, and that means if you see something, say something.
Foster a culture where teams feel safe reporting both successes and concerns - See above, but generally it's a good idea to reward people for reporting, even if you have to grit your teeth while doing so.
Focus on outcome-based metrics rather than operational details - Over the course of a major decision being implemented there will be lots of wins and losses, no big project is perfectly executed. The important things on big projects are momentum and ensuring that you march towards completion.
Build a communications plan for each of the following groups: Staff, executives, customers, board of directors/supervisors. Each group should get regular communication, using a template that ensures you communicate the right focus, details, and metrics to each. The better your communication the less resistance & resentment you’ll face for the changes you are creating.

Staff actions

Prepare detailed analysis of technical requirements and capabilities
Create a structured evaluation frameworks using tools like SWOT analysis that reduce the effort needed to read & understand analysis
Engage key stakeholders early in the decision-making process, multiple departmental experts should already feel consulted and informed.
Outline potential risks and mitigation strategies, what’s foreseeable, and what can be done now or as part of implementation to reduce the impact?
Present multiple solution options with pros and cons, different price points, and different implementation schedules. You want a real spread here.
Prepare contingency plans for potential issues - especially if a major business system might go offline or be unavailable.
Identify what documentation needs to be created, who will make it, and where it will be published.
Identify the training, adoption, and change management work needed to support departments and staff in making use of the results of the decision.

Types of questions you should ask:

What are our business goals & objectives for this work?
How does this work support our strategic plan?
What can we do to reduce risk and/or effort?
What concerns do you have?
What data or metrics will we need to collect in order to evaluate the progress of implementation?
What data or metrics will we need to collect to create a baseline of data to evaluate improvements or reductions in quality after the implementation of this decision?
Does the cost benefit analysis of this decision make sense? I.e. If we are spending $4MM to improve our fundraising platform, how many years of fundraising will it take to recoup that $4MM investment?

Chat with the author

If you'd like to make a connection and perhaps collaborate on something:I'd love to talk with you!No matter if you want to build your professional network,or think there might be a great opportunity to to work together or partner.

Let's connect