New leaders who hold explicit early conversations with the boss about the situation, expectations, working style, resources, and development settle the terms of success before the first contested decision.
An example
Three weeks after an activist investor took a stake in a consumer products company and called for the sale of its household division, a new president arrived to run that division. Before making a single decision, she asked the chief executive for five meetings over her first month. In the first they agreed on the situation: a business to fix, with any sale off the table for at least a year. In the second they set what success would look like by the next annual meeting, two points of margin and a plan for the two weakest brands. The third covered how they would work together, including weekly calls and no surprises on headcount. The fourth was resources, a turnaround team of six and a marketing budget held flat. The fifth was her own development. When the activist pressed for a sale in month four, the chief executive pointed to the agreed plan, and the board backed the turnaround.
Why it works
Later proposals are easier to approve when the terms they will be judged on were agreed before anyone was arguing. Expectations, resources, and the shape of the problem are settled with the boss in calm conversations, and later decisions can point back to them. Leaders who skip these conversations often find, months in, that their boss expected something different, and every proposal then has to fight that gap. A boss willing to commit, candor in both directions, and a habit of revisiting the terms when conditions change are what it needs.
The thinking behind it
Michael D. Watkins The First 90 Days: Critical Success Strategies for New Leaders at All Levels (2003) advises a new leader to hold five conversations with the boss: on the situation, expectations and how success will be measured, working style, resources, and personal development. Watkins treats them as a negotiation that sets the terms on which the leader will be judged. The division president's five meetings follow that design, and the agreed terms are what the chief executive pointed to when the activist pressed.
When it fits
Taking a new role is the moment: a new boss, a new unit, a promotion, a turnaround. The conversations pay off most when the situation is ambiguous, the expectations unclear, or the resources thin. Early access to the boss helps, along with the nerve to ask for explicit answers and a willingness to put the agreed terms in writing.
How to use it well
Hold the conversations early, before the first contested decision, and hold them separately, since each covers a different question.
- Situation: agree on what kind of situation this is, whether a turnaround, a startup, a realignment, or a business to sustain.
- Expectations: agree what success looks like, by when, and how it will be measured.
- Style: agree how you will communicate, how often, in what form, and what the boss wants to hear about first.
- Resources: ask for what the agreed expectations require, and say plainly what will slip without them.
- Development: discuss what you need to grow in the role.
Summarize each conversation in a short note, and revisit the terms when conditions change.
What it costs and where it backfires
Explicit conversations can surface disagreements early, and a boss who prefers to keep options open may resist committing. Asking for resources up front can make you look demanding before you have delivered anything. Terms agreed in writing bind you as well as the boss. Candor is the condition; once you inflate the problem to lower expectations, or bury the commitments in vague language so no one can hold you to them, the agreement stops being useful to either side.
When it is used on you
Expect a new peer who holds an explicit agreement with your shared boss to bring proposals that carry that weight, and consider negotiating your own. If you are the boss, answer the questions honestly. An agreement you do not intend to keep costs you more than a frank refusal.