‘Please sir, I want some more’: why Oliver Twist will never make MD

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‘Please sir, I want some more’: why Oliver Twist will never make MD

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Lobbying for a better bonus is a fine art with high stakes. Most who try it will fail and damage their own prospects.But for those who master it, there is a chance to move up the compensation gears. Here’s how to do it

We’re halfway through November, and the annual process of determining compensation is in full swing at many investment banks. Comp pools are being decided and allocated, and although the final numbers will not be locked down until December and communicated in late January, decisions are taking form now.

This creates a natural question for every investment banker: is this the right moment to signal compensation expectations to my manager? The instinct may be yes, but the task is more fraught than simply making a request.

The difficulty lies not in wanting more, but rather in framing that aspiration in a way that carries weight. Simply saying you would like a higher bonus is weak, much like Oliver Twist asking for more gruel.

To be effective you must present a clear narrative for why your compensation should be reset at a higher level, not merely adjusted at the margins. You also need to introduce a persuasive idea your manager has not already considered. Given the stakes, the standard for a successful conversation is high. The pitch must be built on business logic and retention risk, not on what you’d like.

The pitch must be built on business logic and retention risk, not on what you’d like

The core problem with asking for a larger comp award is that the desire itself is obvious. Your boss already knows you want to be paid more. Everyone does. Stating it openly adds nothing and arguably signals insecurity. It turns what should be a commercial discussion into a plea.

Actually, it’s worse than that. This kind of framing keeps your manager focused on the challenge of distributing limited funds rather than on the strategic value you bring. When I was being buffeted with comp talk, I would instinctively try to manage down expectations in everything I said to the team. That’s not what you want to hear in reply to your pitch.

The aim should not be to secure a slightly bigger increase than last year but to make a grounded argument for rebasing your compensation to a level that represents your current and future contribution to the firm. This shifts the discussion away from what you feel you deserve and towards what the market would pay for someone in your role with your impact.

Building such an argument requires a deliberate change in viewpoint. You must either tell your boss something they haven’t fully appreciated, or present familiar information in a sharper, more strategic way. A manager can reasonably be irritated if you simply list deals they’ve already approved or repeat revenue figures they’ve already seen — “Tell me something I don’t already know,” they can legitimately cry. Doing so can also appear patronising because it suggests they’re inattentive and they don’t have visibility on what you’re doing.

The better approach is to move from the transactional to the forward-looking. Don’t just recap the deals you executed. Show how your efforts have strengthened relationships that position the team for future mandates not yet visible in current numbers. Explain how you have mentored juniors in a way that has improved team culture or enhanced connectivity across different groups. Point out any original analysis you produced that helped identify a new revenue path or something you did to avoid a significant financial or reputational loss. Highlight contributions that create value over time rather than for a single moment.

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It should be a positive conversation, not a whine and a whinge

This change in framing alters the tone of the discussion. You don’t want to come across as a subordinate supplicant seeking a favour, but rather as a valuable asset asking for a revaluation. The most important part of the pitch is making it clearly in your manager’s interest to retain you.

Most of all, don’t come across as entitled or aggrieved, even if you think you’ve been underpaid or underappreciated in past years — if you were underpaid, why didn’t you move?

You should give the impression of being confident but not arrogant, in command and with no chips on your shoulder. It should be a positive conversation, not a whine and a whinge.

The lingering question is whether it is worth having this discussion at all. The answer is qualified yes, but only if your preparation is rigorous. If you can’t bring something new, concrete and strategically important to the table, silence may be wiser. A weak request can damage your credibility and mark you as unaware of the commercial pressures your manager faces or the competitive environment in which the team is operating.

Asking for more gruel is never a strong position. If your case is only a restatement of your job description, it will not help you. However, if you can construct a narrative that reframes your value, aligns your compensation with your manager’s objectives and demonstrates the mutual benefit of investing in your continued growth, then now is your chance to speak up. A seat at the top table and a succulent roast dinner awaits.

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