Ask about overlapping roles before judging the CV

A founder once asked me what warning sign I look for when reviewing designer portfolios. My answer started outside the portfolio: I look at the CV timeline. Two positions with overlapping dates raise a question about what the person was doing and how the work was arranged.

My original post framed overlap strongly as a capacity concern. The more useful version of that advice is to ask before judging. Overlapping dates can describe consulting clients, part-time work, a transition between jobs, an advisory role, or an imprecisely maintained profile. They can also reveal a commitment problem. The dates alone do not tell you which explanation applies.

Use the timeline to identify a question, then assess the answer against the needs of the role. A shortcut that replaces context with suspicion will reject some good candidates for the wrong reason.

Establish what each role actually was

A CV compresses a career into labels and dates. “Lead Designer” does not tell you whether the arrangement was full-time employment, a two-day-a-week engagement, or a limited project. Two labels that look equivalent on the page may describe very different commitments.

Ask the person to walk you through the period. What was the arrangement for each role? How much time did each require? Were the clients or employers aware of the commitments? What responsibilities did the designer personally carry?

Keep the question neutral. You are trying to understand a working arrangement, not obtain a confession. If a profile lists months rather than exact dates, even a clean transition can look like an overlap. Give the candidate a chance to clarify the record before treating the presentation as evidence of a problem.

Recognize legitimate concurrent work

Independent designers may serve multiple clients. A person may teach alongside a product role, advise a company occasionally, or finish a limited handover while beginning another engagement. A founder may continue listing a business they own after their daily involvement has reduced.

These arrangements can be entirely compatible with good work. The relevant issue is whether the expectations, availability, and responsibilities are clear. A contract for a defined contribution should not be assessed as though it implicitly promised exclusive full-time attention.

Ask what the overlap meant in practice. Did the work happen in separate blocks? Were there predictable deadlines? How were urgent requests handled? The explanation should help you understand capacity without requiring disclosure of confidential client information.

Evaluate capacity in relation to your role

The hiring question is not whether a person has ever had more than one professional commitment. It is whether they can meet the requirements of the arrangement you are offering.

Describe those requirements explicitly. How much availability does the team need? Are there important working hours? Does the role require sustained product context, frequent collaboration, or responsibility for decisions that cannot wait several days? Which expectations are essential, and which simply reflect the team's current habits?

Then ask how the candidate's planned commitments fit. A person may be ending one engagement before starting another. They may want to retain a small amount of outside work. You need an honest conversation about the proposed future arrangement, not just an interpretation of dates from years ago.

Ask for evidence about the work itself

If you are concerned about whether the person was able to contribute meaningfully during an overlap, return to the projects. Ask what they owned, which decisions they made, and how they stayed informed as the work changed.

Look for a coherent account of collaboration and delivery. Who depended on their work? How did they manage competing deadlines? What did they do when a commitment became unrealistic? A candidate who can describe a difficult trade-off and how they addressed it may provide more useful evidence than one whose dates happen to look tidy.

Do not infer effort from the number of portfolio pieces alone. Some work is confidential, some projects take longer than expected, and a short engagement can involve a significant contribution. Assess the explanation and the relevant evidence together.

Distinguish unclear presentation from a substantive concern

Sometimes the answer is simply that the CV needs a better label. Adding “contract,” “part-time,” or a brief explanation of a transition can remove ambiguity for future readers. That is a presentation issue.

A more substantive concern would involve an unresolved mismatch between the commitments described and the availability the person is promising now. Another would be materially inconsistent explanations that the candidate cannot clarify when given a fair opportunity.

Record the specific issue rather than writing “red flag” and moving on. What is uncertain? Why does it matter for this job? What evidence would resolve it? If the answer is already sufficient, do not keep escalating the question because the original impression was negative.

Give candidates a clearer way to present their timeline

For designers, the practical advice is to make concurrent work understandable. Label the engagement type where it matters, keep dates accurate, and add a short note when a role continued in a reduced capacity.

You do not need to publish private contract terms or defend every month of your career. You do need to help a reader understand the relationship between the roles. A small amount of context can prevent a compressed timeline from telling the wrong story.

Be equally clear about what you are seeking next. If you want employment, explain your transition. If you want a consulting engagement, describe the availability and scope you can offer. That makes it easier for a company to assess a real arrangement instead of an imagined one.

I still look at the dates. They help me ask questions the polished case study may not answer. But the decision should come from the explanation, the work, and the commitments both sides are prepared to make, not from the overlap by itself.