Leaves in the gutters seem like a small job until water starts running over the edge onto the path or the front step. Clearing them is worth doing before the cold months, when wet leaves freeze and push water into places it should not go. The real question is not whether to clear them, but who does which part.
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Look at the house from the ground first
Walk all the way around. Note how many stories the gutters run along, how steep the roof looks, whether there are power lines close to the eaves, and whether the ground is soft or uneven where a ladder would stand. Look for sagging sections, loose brackets, and downspouts that are blocked or disconnected at the bottom. Notice whether water comes over the front edge in rain, or whether the gutters look clear from below and are full inside.
Decide what he can do from the ground
Some of the work does not need a ladder. A long-handled gutter scoop or a sturdy scoop on a pole can clear the lower sections if they are within reach from the ground. Downspout flushing with a garden hose from the bottom can show whether water is draining properly. If he can do this safely from where he stands, it may be the only part of the job that needs doing.
Decide what needs someone else
Hire it out if the gutters run along a second story, if the roof is steep, if the ladder would need to reach the eaves from uneven ground, or if the job would be his first time on a ladder in years. The same goes for gutters that sag, pull away from the house or have damage, because clearing them is only part of what needs fixing. Ask a professional to look at those sections and report what they find.
What to ask a gutter company
Ask what the price includes: removing debris from the property, flushing downspouts, and whether they take the leaves away or leave them on the ground. Ask how they will access the roof and whether they will use a ladder, a platform or a lift. Ask whether they carry liability insurance and workers' compensation, and ask for a certificate. Then call the insurer named on it to confirm it is current. Ask what they do if they damage a gutter or a shingle, and whether that is covered by their policy. Ask whether they will send a written report of anything they find that needs repair, with photos.
What to do tonight
If the gutters are only a little full and the ground-level parts are reachable, clear what you can with a scoop and check the downspouts with a hose. Leave the upper sections alone and write down what you saw from the ground. If you see sagging or water spilling over the edge, that is your reason to call for a written quote before the rain comes.
Keeping the decision simple
Decide once which part he does from the ground and which part a company does, then write that down on the calendar by the phone so the next person who visits knows the plan. You can use the same split every year and only change it when the house or the ladder changes.