by Charlie Loulakis, Chief Growth Officer | 5 Minute Read

Organizations invest significant time, money and resources into managing and delivering on their top priority initiatives. But many still struggle to consistently deliver value through their portfolio that achieve desired business results.

Why does this disconnect occur? Often, it stems from a portfolio not tightly aligned to overarching strategic goals and outcomes.

When your initiative mix doesn’t directly map to achieving your most important objectives, delivering meaningful value becomes difficult. Resources get spread thin across disconnected, potentially low-impact initiatives.

True strategic alignment means your portfolio should shift as company priorities evolve. You need to say “No” to initiatives that no longer map to current goals. New investments need to go to initiatives targeting the strategic needs of today and tomorrow.

So, how can you make this happen?

Let’s explore key signs your portfolio may lack strategic alignment, as well as how to assess and fix misalignment issues. With consistent monitoring and adjustment, our goal is to build your portfolio into a clear and transparent value delivery vehicle by understanding your key outcomes, aligning delivery strategy, and learning to say no to limit work in progress.

Warning Signs Your Portfolio Lacks Strategic Alignment

How do you know if your initiative portfolio is disconnected from strategic goals? Watch for these common warning signs:

There is no clear priority, and leaders tend to disagree on what initiatives are most important.
Your initiatives aren’t tied to clear business outcomes or customer needs you want to accomplish.
You rarely say no, or when you do, you’ve already invested significant capital in the initiative.
There are too many active initiatives for organization capacity.

Your goalpost for initiative completion continues to move, creating a portfolio with many large, never-ending bodies of work.
Employees don’t understand how their work links to strategic outcomes.
Strategic objectives are not met at the end of the fiscal year.

You Know Your Portfolio Has a Problem, Now What?

If you see misalignment signs, take time to formally assess how well your portfolio maps to strategic goals. This analysis is crucial.

First, start by clearly defining your key organizational objectives and desired outcomes for the next 1-3 years. Be specific on what success looks like. This becomes your north star for the WHY behind the work you need to accomplish. Common goals include:

Increasing market share by X%
Improving customer satisfaction scores to X
Growing online sales by X%
Reducing technology costs by X%

Next, now that we know why we are doing the work we are doing, we need to understand WHAT initiatives can help us achieve those goals. One way is to conduct an objective audit of your portfolio and build a framework for prioritizing the work based on the impact it will have on our goals. Assess each active or proposed initiative, asking questions like:

What strategic goal(s) does this initiative directly advance? How specifically?

What measurable impact will this initiative deliver toward that strategic goal if successful?
Is this initiative’s scope aligned to producing that specific outcome?
Does this initiative carry more weight and urgency than any other potential initiatives based on our current strategic needs?
What value does this initiative deliver, what are the risks involved, and what is the size of the effort to achieve that value?

Be fully honest. Initiatives unable to be clearly justified against the strategic goals warrant pausing or cancelling altogether. Leveraging a specific prioritization framework like WSJF can be a useful tool for creating clear alignment.

Third, now that you have an updated prioritization and alignment, it is time to right-size your portfolio. This is the hardest part, because it requires learning to say no to the right things so your people can focus on delivering value in the right areas. Our goal is to focus on the highest strategic initiatives by limiting the work in progress in our portfolio.

Ongoing Maintenance: 8 Steps to Improve Flow Through Your Portfolio Kanban

Now that you’ve realigned your Portfolio, the key is to build in quality to make sure that you are consistently working on the right initiatives at the right time.

Review and assess how work gets from ideation to execution within your portfolio and build in exit criteria along each step to make sure that you can do the right amount of discovery, analysis, and decision making at the right time.

Clarify and Communicate Strategic Priorities: Leaders must align on the vital few objectives for the organization right now. Communicate focus areas clearly and repeatedly across teams.
Continuously Prioritize All Initiatives: No initiative gets a free pass. Re-validate every initiative against the strategic goals to work on the right work.
Align People to Value: Moving budgets and talent to initiatives directly driving strategic success is crucial, even if difficult. Demonstrate this priority through resourcing decisions.
Set Portfolio Guardrails: Define portfolio constraints around total budgets, headcount, number of active initiatives, initiative categories, etc. to keep alignment intact going forward. Invest in a good mix of innovative ideas, cost saving initiatives, and building out your architectural runway.
Increase Visibility: Give decision-makers and employees increased visibility into initiatives and how they map to objectives. This drives engagement and accountability.
Learn How to Say No: Split or descope initiatives that have ballooned beyond their original aligned scope. Large, endless initiatives prevent results. Don’t overcommit.
Update Processes: Build selection/prioritization processes ensuring new initiatives align to strategic goals. Prevent misaligned ideas from ever entering your portfolio.
Continuously Reflect and Adjust: Your initiative portfolio is a dynamic, living system. As strategies evolve, re-validate and adjust your portfolio accordingly.

Achieving alignment is an ongoing journey. But with consistent, objective analysis of initiatives against goals, your portfolio will transform into a engine for delivering tangible value, quarter after quarter.

Key Takeaways

Misalignment between initiative portfolios and strategic goals is a top reason organizations fail to meet objectives.
Warning signs include too many initiatives, unclear initiative outcomes, and post-completion lack of impact.
Assess initiatives against specific strategic goals to identify mismatches in scope, priorities, and resourcing.
Right-size your portfolio by refocusing on the vital few objectives, shifting resources, and strengthening guardrails.
Maintain alignment through clear communication, increased visibility, and continuous monitoring of initiatives against evolving strategy.

With your portfolio and organizational strategy in lockstep, executing your most important goals becomes smoother, faster, and more impactful. Initiatives turn into levers for accelerating strategic success.

Looking for support in improving the way your portfolio ideates, evaluates, and delivers on your top priorities? Reach out and let’s get the conversation started!

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