Chefen borde ha följt upp framstegen tidigare.

It is a modal verb + perfect infinitive structure.

• borde = should / ought to
• ha följt upp = have followed up

So borde ha följt upp means should have followed up.

This structure is used when talking about something that would have been the right thing to do in the past, but did not happen, or may not have happened.

Because the sentence refers to a past action.

• borde följa upp = should follow up / should be following up (present or future sense)
• borde ha följt upp = should have followed up (past sense)

So if you want to say that the boss ought to have done this earlier, Swedish uses:

• borde + ha + supine

Here, the supine is följt.

Because följa upp is a particle verb, similar to an English phrasal verb like follow up.

Its basic parts are:

• följa upp = to follow up

In some forms, the particle upp stays separate:

• att följa upp
• har följt upp
• borde ha följt upp

This is normal in Swedish. The particle often comes after the verb form, just as in English follow up.

Följt is the supine form of följa.

In Swedish, the supine is used with ha to form perfect-type constructions:

• har följt upp = has/have followed up
• hade följt upp = had followed up
• borde ha följt upp = should have followed up

Do not confuse the supine with the past participle:

• supine: följt
• past participle: följd, följt, följda in other contexts

In this sentence, after ha, Swedish uses the supine.

Because chefen means the boss.

Swedish usually puts the definite article at the end of the noun:

• en chef = a boss
• chefen = the boss

So -en here is the definite ending.

Framstegen means the progress or the advances.

It comes from:

• framsteg = progress / advance / step forward
• framstegen = the progress / the advances

A useful thing to know is that framsteg is often treated as a plural-looking noun in form, even when English would simply say progress.

So:

• göra framsteg = make progress
• följa upp framstegen = follow up on the progress

Because the sentence refers to specific progress that is already understood in context: the progress.

Compare:

• följa upp framsteg = follow up progress / follow up on progress in a more general sense
• följa upp framstegen = follow up the progress

The definite form framstegen points to progress that has already been mentioned or is known from the situation.

Here, tidigare means earlier.

So:

• tidigare = earlier
• senare = later

In this sentence, tidigare tells us that the follow-up should have happened before it actually did, or before now.

In this sentence, tidigare comes at the end:

• Chefen borde ha följt upp framstegen tidigare.

That is a very natural position for a time adverb.

You can sometimes move adverbs for emphasis, but the original version is the most neutral and idiomatic. For example:

• Chefen borde tidigare ha följt upp framstegen.

This is possible, but it sounds more formal or marked. For most learners, the end position is the safest choice here.

Yes, usually.

borde ha often suggests that something would have been better or more correct, so it can sound like criticism, regret, or hindsight.

So this sentence suggests:

• the boss did not follow up early enough
• that was probably a mistake or a missed responsibility

It is similar in tone to English The boss should have followed up on the progress earlier.

Because Swedish does not always match English word-for-word.

English often says:

• follow up on the progress

Swedish simply says:

• följa upp framstegen

The meaning of follow up is already built into the particle verb följa upp, so Swedish does not need a separate word corresponding exactly to on here.

Följt upp is very natural, especially in work, management, school, and project contexts.

But there are alternatives depending on nuance:

• Chefen borde ha kontrollerat framstegen tidigare.
  = The boss should have checked the progress earlier.

• Chefen borde ha sett över framstegen tidigare.
  = The boss should have reviewed the progress earlier.

• Chefen borde ha hållit bättre koll på framstegen tidigare.
  = The boss should have kept better track of the progress earlier.

Still, följa upp is especially common when talking about monitoring or checking results over time.

The sentence follows normal Swedish main-clause word order:

• Chefen = subject
• borde = finite verb
• ha följt upp = infinitive/perfect infinitive part
• framstegen = object
• tidigare = adverb

So the pattern is roughly:

Subject + finite verb + infinitive elements + object + adverb

A key rule in Swedish main clauses is that the finite verb usually comes in second position. Here that finite verb is borde.

A yes/no question would usually invert the subject and the finite verb:

• Borde chefen ha följt upp framstegen tidigare?
  = Should the boss have followed up on the progress earlier?

This is a good example of Swedish verb-second behavior: in a question, the finite verb borde comes before the subject chefen.

Not usually if you want the meaning should have.

• borde ha följt upp = should have followed up
• skulle ha följt upp usually means would have followed up

So they are different:

• Chefen borde ha följt upp framstegen tidigare.
  The boss should have followed up earlier.

• Chefen skulle ha följt upp framstegen tidigare.
  The boss was supposed to / would have followed up earlier, depending on context.

So borde is the correct choice for advice, criticism, or obligation in hindsight.

A rough guide for an English speaker might be:

SHEF-en BOR-de hah FYELT up FRAM-stay-gen TEE-di-ga-re

A few notes:

• ch in chefen sounds like sh
• fö has a vowel not found exactly in English; it is somewhat like fur but with rounded lips
• sj is not in this sentence, so pronunciation is a bit easier than in many Swedish words
• stress is mainly on:
  • CHE-fen
  • BOR-de
  • följt UPP
  • FRAM-stegen
  • TIDigare

A more accurate pronunciation would depend on dialect, but that rough version is a useful start.