Five Ws Plus How, Career Scaffold

Dimension: Direction · Type: Stage

Six question prompts (Who, What, Where, When, Why, How) for breaking career-related analysis paralysis into a finite list of things to find out. The point is not the questions themselves; the point is to get them out of your head and onto paper, so vague anxiety becomes a list you can act on.

Introduced by Liz Oseland and Hannah Nash (10Eighty) at the Own Your Future, Make Your Role Matter session of the UN Inter-Agency Career Week 2026, on 8 May 2026. Liz framed the scaffold as the operational counter-move to analysis paralysis: get the questions out of your head and onto paper. Hannah reinforced the Who dimension repeatedly throughout the session. The underlying structure (Five Ws + How) is the standard journalism and problem-solving heuristic.

The framework

The structure is deliberately permissive. Any question that comes to mind goes under the right column. The questions are unique to you; they will not be the same as anyone else’s.

When to use it

• When you are stuck on a career question and the loop in your head has stopped producing answers.
• When you keep saying “I do not know what to do” and want a structured way to surface what you actually do not know.
• Before a coaching session, a mentor conversation, or a meeting with HR, to bring specific questions rather than generic ones.
• After running the Intelligent Career Model or Four-Loop Alignment and wanting to convert the diagnosis into a list of next steps.
• When supporting a colleague who is overwhelmed and cannot tell what to do next.

What you need

Pen and paper or a notes document. The exercise loses most of its effect done in your head. 30 to 45 minutes of quiet, or a 15-minute version with a trusted person. Optional: a specific career question you are sitting with.

The six prompts

Who. Who can help me with this? Who would have the perspective I am missing? Who can I tell about my purpose so they can keep an eye out? Who do I need feedback from? Who is doing what I am thinking of doing, that I could learn from? Who has changed what I am thinking of changing?

The Who column is usually the most underused, and is also where most career movement actually originates. The session was emphatic on this dimension. Most people invest deeply in the What and the How and barely at all in the Who.

What. What tasks could I take on that would build the skill or visibility I need? What roles are there that I might not have considered? What stretch assignments could I propose? What skills could I lean on that I am currently underusing?

The What column converts vague ambition into concrete actions you could take.

Where. Where can I get more exposure or visibility? Where are the conversations happening that I am currently not in? Where are the opportunities I do not know about (other agencies, regional offices, communities of practice, conferences)? Where would my profile sit better than where it sits now?

When. When are the opportunities coming? When is the next budget cycle, the next mobility window, the next round of secondments? When does my contract end and what is my preparation timeline? When am I going to do the next concrete thing on this list (a date, not “soon”)?

Why. Why does this matter to me? Why am I considering this change now and not six months ago or six months from now? Why this organisation, this role, this direction? Why am I stuck in the way I am stuck?

The Why column is the one that often re-grounds the exercise when the other columns produce a long task list with no purpose attached.

How. How do I move? How do I volunteer for the stretch assignment? How do I tell my supervisor about my direction without creating awkwardness? How do I find out about the JPO programme, the secondment options, the upcoming reorganisation? How do I upskill in AI, in data, in the area I have been deferring?

The How column is where the questions become operational. Each How is a thing you can go answer.

Steps

1. Take the prompts in any order. Some people work better starting with Why, others with Who. The order does not matter.
2. Write every question that comes to mind. Do not edit. Do not pre-judge whether a question is “good”. The unfiltered list is the raw material.
3. Group into columns. Each question goes under one of the six headings.
4. Check coverage. Is one column conspicuously empty? That is often the dimension you are avoiding. Spend an extra five minutes adding questions there.
5. Mark the three to five questions you most need answered. Out of the long list, choose the small set that would open up the most.
6. For each chosen question, name the next concrete action. Not “think about this”. A specific thing you will do this week, with a date.
7. Run the actions. The scaffold’s value is in the conversion: from vague anxiety to a finite list to specific moves you can complete.

Worked example

A staff member is stuck. Her contract ends in nine months. She has been thinking about a sector pivot. She has not done anything concrete in three months. She runs the Five Ws + How scaffold.

• Who?
  • Who in my network has made a similar pivot in the last three years?
  • Who could give me honest feedback on whether my profile would land in the new sector?
  • Who is currently working in a role I would consider taking?
  • Who in my own agency might be a sponsor if I want to stay?
  • Who would I tell first about my direction if I was honest about it?
• What?
  • What three roles in the new sector would I credibly apply for?
  • What stretch assignments in my current role would build the skills I need?
  • What’s missing from my CV that the new sector would expect?
  • What experience do I have that would translate but I am not currently surfacing?
• Where?
  • Where can I see vacancies in the new sector that I am not seeing now?
  • Where are the relevant conferences or communities of practice?
  • Where would my profile be more competitive: the same sector at a different agency, or a related sector entirely?
• When?
  • When does my contract actually end (exact date)?
  • When are the next two recruitment cycles in my agency and in two adjacent ones?
  • When do I need to start applying to land a role before my contract ends?
  • When this week am I going to send the first message?
• Why?
  • Why am I considering a pivot rather than staying?
  • Why now and not in three months?
  • Why this sector and not the adjacent one?
• How?
  • How do I find out which agencies are recruiting for my profile?
  • How do I update my LinkedIn so the new sector recognises me?
  • How do I use the JD Colour-Coded Breakdown on a real vacancy to test whether my profile lands?

She marks the three questions that would open up the most: who in her network has made a similar pivot, what three specific roles she would credibly apply for, and when she will send the first message. She names a concrete action for each: a Tuesday-morning slot to message two people, a Saturday-morning slot to do the JD colour-coding on three roles she has been watching, and a date for the first message.

The vague anxiety is now a finite list. She stops looping. She acts.

Pitfalls

• Doing it in your head. The scaffold loses most of its effect. Write.
• Producing a long list and not converting to actions. The exercise has two halves: the surfacing and the conversion. Stopping at the surfacing produces a longer list of things you do not know, which is not the same as a shorter list of things you will do.
• Skipping the Who column. This is the single most common pattern. Most people instinctively go to What and How and never deliberately list Who.
• Pre-judging questions as “stupid”. “I should already know this” is the kind of comment that keeps a question off the list and blocks the answer. The unfiltered version is the working material.
• Confusing the scaffold with a complete plan. Five Ws + How is for getting unstuck and for surfacing what you do not know. It is not a strategic plan. Pair with Intelligent Career Model and Four-Loop Alignment for the upstream direction work.
• Running it once and not returning. The list ages. Re-run after each significant action; the questions shift as you learn.

When not to use it

When you are in acute distress and the question is not really “what should I do” but “how do I cope with this right now”. Run regulation tools first (Body Scan, Progressive Muscle Relaxation). The scaffold is for clear-headed unsticking, not for acute regulation.

When you have a clear direction and a clear plan; the scaffold is for stuck moments, not for execution. If you know what you are doing, the right tool is habit installation for follow-through, not another round of question generation.

When your stuckness is actually about a values question or a meaning question. The scaffold surfaces operational questions; if the underlying issue is “I am not sure what I care about anymore”, run the Five Whys for Purpose exercise first.

How I use it

Personal note pending. Davide to fill.

Related frameworks

• Intelligent Career Model, the upstream diagnostic that often surfaces the dimension this scaffold then operationalises.
• Four-Loop Alignment, the alignment exercise that often produces the questions the scaffold then organises.
• Five Whys for Purpose, the upstream tool when the stuckness is about meaning rather than operations.
• 3 to 5 Key Result Areas, the prioritisation tool for the actions the scaffold surfaces.

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Notes compiled by Davide Piga. Last updated 2026-05-09.