How to Perform Effective Midyear Check-ins

At Prodify, we've observed that while companies invest heavily in annual planning, midyear check-ins often get overlooked. But, these check-ins are crucial for ensuring you are achieving outcomes.  We want to avoid spending a year building and launching projects only to look back and find they didn't achieve the desired outcomes and the business is no further along than a year ago.

Why do Midyear Check-Ins?

Midyear is the perfect time to assess progress and recalibrate:

• You're 50% through the year and thus ideally ~50% towards annual goals
• Enough time has passed for each pod to demonstrate significant impact
• Your perspective may have shifted since the year's start
• New information can inform second-half strategies
• It's not too early to start thinking about next year
• An interim review can build momentum for future planning

Midyear Check-In Evaluation Criteria

The goal is to evaluate the past in order to learn from it and apply those learnings to the 2nd half and future. The below table summarizes an approach for this.

Now, let’s dig deeper into each aspect. 

Plans & Progress

H1 Evaluation: Progress vs. Annual Plan 

Create a scorecard of Q1 and Q2 key outcomes and KPIs. With your team, mark each as met, exceeded, or missed. 

Key questions:

• Which objectives were met, exceeded, or fell short? 
• How do actual results compare to projections?

Document success factors and key challenges to inform your strategy for the second half. If your team didn’t have clear objectives and/or make material progress in the past six months, this should be a signal to understand why and evaluate changes to your approach going forward.

H2 Adjustments: Refreshed H2 Plan

Reflect on successes and challenges to adjust your 2nd half plan.

Key Questions:

• What key outcomes are we targeting for the rest of the year?
• Does our current plan support these outcomes and reflect our recent learnings?
• Can we be more aggressive (especially where we exceeded H1 goals) or do we need to be more conservative (especially where we missed H1 goals)?
• What should be added or removed from our plan?

Collaborate with your product cross-functional team and stakeholders to ensure clarity on decisions and how the refreshed plan will achieve shared outcomes.

Future Year(s) Planning: Vision and Strategy Review

Account for learnings from the current year, market shifts, customer research, and new opportunities.

Key Questions:

• How does our trajectory align with our long-term product vision?
• What industry trends or disruptions should we prepare for?
• Do our first-half learnings suggest vision adjustments or reinforcement?

Identify potential vision adjustments or plan further research, particularly to inform upcoming strategic phases. Include stakeholders to ensure clarity on vision and strategy shifts. Reinforce with your team to maintain alignment with longer term plans and remind them of how their work connects to that.

Team

H1 Evaluation: Performance Discussions

Reflect on how well the teams have been set up for success. For the purpose of this article, we will focus on reflecting on the overall organization. We do consider performance reviews and ongoing feedback important, but that is a larger topic that can have its own deep dive. 

Key Questions:

• Did the product team have all the resources and context they needed to deliver?
• Were there any skill gaps that impacted our ability to deliver?
• How well did cross-functional collaboration work to drive towards a successful product?
• Which teams made the most – and least – progress, and what can be learned from this? 

Use these insights to identify areas where you can support the team and remove blockers.

H2 Adjustments: Staffing Rebalancing

Consider changes in team allocation to better achieve goals.

Key Questions:

• Are resources properly allocated to support top priorities and biggest opportunities?
• What critical training or hiring is needed to address skill gaps?
• How can we improve cross-functional collaboration?

Implement changes based on your answers to set each team up for greater success.

Future Year(s) Planning: Org Structure Evolution

Assess if your team structure supports upcoming milestones of the product vision. The evolution of an organizational structure may take longer to evaluate and plan, but reviewing now can inform future plans.

Key Questions: 

• Does our team structure balance focus on our long-term vision with short-term goals?
• Is there an appropriate mix of leadership and individual contributors across levels?
• Do we have the right proportions of PMs, engineers, designers, analytics and other pod functions for our product's complexity and to enable greater pod impact?
• Is the prod-dev team structured well to do their work with high autonomy and minimal reliance on other teams?

Use these insights to prepare for potential hiring needs or larger team evolution heading into next year.

Process

H1 Evaluation: Team Retrospectives

Conduct team retrospectives to assess if you're focused on impactful work and approaching it in an effective way. Be honest in your assessment to drive improvement.

Key Questions:

• How effective was our prioritization process in focusing on the most impactful problems?
• Did we balance short-term fixes and long-term strategic initiatives effectively?
• Did each team have sufficient focus to understand customer needs, iterate on results, and make meaningful progress against top priorities?
• What were the key factors in how we approached successful projects, and primary reasons for those that fell short?

Identify the top 3 improvement areas to focus on for H2 based on these learnings.

H2 Adjustment: Product Operations Priorities

Apply key learnings from the retrospective to improve effectiveness in H2. Engage your team to ensure buy-in.

Key Questions:

• How can we apply our H1 learnings to enhance effectiveness in H2?
• In what ways can AI improve our efficiency and free up time for strategic work?
• How can we validate projects faster and at lower cost to improve our success rate and invest proportionate to our confidence?

Document planned changes with specific action items and owners, and consistently address them in team meetings and 1 on 1s to ensure follow-through.

Future Year(s) Planning: Plan for Scalability

Plan for scalability, keeping the product vision in mind. Partner with engineering and other cross-functional stakeholders.

Key Questions

• What scalability needs (performance, security, internal tools) should we consider for each successful initiative?
• Which items are critical to start soon?
• What milestones should trigger the implementation of other scalability items?

Collaborate to ensure alignment on the vision and each team's role in fulfilling it.

Conclusion

To be clear, we are not saying to only check in midyear and not before that. You should be doing smaller, more frequent check-ins with your team on progress throughout their work. These help monitor progress and provide support throughout. And you should be giving ongoing performance feedback, highlighting both positive things to reinforce and areas for improvement. If you wait 6 months to do your first assessment of how things are going, you miss numerous opportunities for more timely and less disruptive adjustments.

However, midyear is a nice time to do a deeper dive reflection on the first half of the year in order to modify plans for the second half, and identify potential changes to the product vision. There is overhead to reviewing and planning processes, so we recommend striving for a balance of frequent, lightweight adjustments and episodic, more thorough evaluations.

As you implement these check-ins, you'll find your team becoming more agile, more focused, and more effective at delivering value to your customers and business. So take the time to pause, reflect, and realign - your future self will thank you when you're celebrating your end-of-year achievements and confidently planning for the years ahead.

(Blog was written by Sara Zalowitz with collaboration with David Jesse)